RU2662778C2 - Water-insoluble cyclodextrine polycondensate: application as a capturing agent - Google Patents

Abstract

FIELD: hygiene.

SUBSTANCE: water-insoluble cyclodextrin polycondensate is proposed which is prepared by mixing at least one cyclodextrin and at least one saturated or unsaturated or aromatic, linear or branched or cyclic polycarboxylic acid and / or at least one ester, or one acid anhydride, or one acid halide of said polycarboxylic acid and at least one thermoplastic polyol polymer. Mixing is carried out in an apparatus functioning with a shearing force sufficient to bring said mixture into a thermoplastic state at a temperature of from 100 to 250°C.

EFFECT: invention provides a highly effective substance used as an agent for capturing a wide range of substances.

32 cl, 10 tbl, 1 ex

Description

The object of the present invention is a water-insoluble cyclodextrin polycondensate, which can be obtained by the esterification / polycondensation reaction:

(A) at least one cyclodextrin; and

(B) at least one saturated or unsaturated, or aromatic, linear or branched or cyclic polycarboxylic acid and / or at least one ester or one acid anhydride or one acid halide based on said polycarboxylic acid, and

(C) at least one thermoplastic polyol as one polymer and

(D) optionally at least one esterification catalyst and / or

(E) optionally at least one cyclic polycarboxylic acid anhydride selected to be different from the polycarboxylic acid anhydride of paragraph (B), and / or

(F) optionally, in the presence of at least one non-polymeric polyol containing from 3 to 6 hydroxyl groups.

The present invention also relates to the use of such cyclodextrin polycondensates as capture agents for a wide variety of substances in many technical fields.

The objective of the present invention is to search for new substances that allow capture into a matrix consisting of a very wide range of substances or mixtures of substances, for example, substances that can pollute the environment, substances that can have a negative effect on various consumer goods in many industries or in the field of cosmetics, and substances capable of causing, for example, unwanted interactions with the keratin substance, in particular with the human keratin substance.

The next objective of the present invention is also to search for new materials that capture at least one useful agent and slow down the rate of its release into the environment, so that

(i) either protect it, for example, during its storage or during its transportation, in order to prevent its destruction, for example, under the influence of atmospheric factors such as heat or cold, temperature changes, ambient humidity, atmospheric oxygen, or UV radiation.

(ii) or, in addition, isolate it and prevent or slow its contact with one or more other ingredients of the composition, or the area to which it needs to be applied, with which it is incompatible,

(iii) either capture it and extend the time it is released from the capture agent in order to increase its effectiveness and / or its stability and / or its deposition in the area in which it is to be applied.

Among the useful agents used, in particular in the cosmetic or pharmaceutical industry, in perfumery, in the food industry or in products manufactured by the textile or leather industry, in particular in textile or other materials or in cleaning products, perfume should be especially mentioned, flavored essences, essential oils, bleaches, insecticides, dyes, lipids, silicones, waxes, flavors, enzymes, oxidizing agents, microorganisms, phytosanitary active agents, food additives and, such as flavor enhancers, fabric softeners, bactericidal agents, coolants, active ingredients of drugs, and cosmetically or dermatologically active substances. Typically, such beneficial agents are expensive and / or volatile and / or physically chemically unstable and / or effective for too short periods of time. Therefore, there is a need to optimize their quantity in order to reduce costs, increase their sustainability, protect them from their environment and / or increase their efficiency over time.

One way to solve these problems, known from the prior art, is microencapsulation of these substances. In addition to the previously mentioned advantages, such encapsulation also simplifies the use of this substance by diluting it and ensuring its homogeneous distribution in the carrier.

Microencapsulation combines all methods of coating or capturing substances in solid, liquid or gaseous form into separate particles, the size of which varies in the range from several microns to several millimeters. In the case when these particles are hollow (vesicular), they are called microcapsules, and in the case when they are solid (consisting of particles), they are called microspheres. Their size varies from 1 μm to more than 1000 μm. These microparticles may be biodegradable or biodegradable, and may contain from 5% to 90% (by weight) of the encapsulated substance.

Encapsulated substances vary greatly in origin: pharmaceutically active ingredients, cosmetically active ingredients, food additives, phytosanitary products, flavored essences, microorganisms, cells or chemical reaction catalysts and so on.

The complete advantage of these known microcapsules is the presence of a polymer membrane that isolates and protects the contents from the external environment. If necessary, the membrane will break down during use, releasing contents (for example, rub and smell advertising inserts that release a fragrance when microcapsules are destroyed), or the membrane will remain in the process of releasing contents, the diffusion rate of which it will control (example: encapsulation of drugs agents for slow release).

The main methods of the preceding field for the encapsulation of substances in microparticles are polymerization at the phase boundary, crosslinking at the phase boundary, an emulsion followed by evaporation or extraction of the solvent, evaporation of the solvent / extraction from the double emulsion, freeze drying, prilling, coacervation and so on.

Also known are microbeads consisting of hydrophobic polymeric materials, which are usually made by phase separation methods (coacervation or extraction-evaporation of the solvent) or polymerization or polycondensation. As a rule, in the phase separation method, organic solvents are used, which have a certain number of disadvantages: emission into the atmosphere, long-term storage in galenical systems, denaturation of some microencapsulated molecules. Currently known methods of polymerization or polycondensation have the disadvantages of using highly reactive substances that can interact with substances encapsulated within these microbeads.

Microbeads obtained from hydrophilic polymeric materials, which are usually prepared by gelation or coacervation, are also known from the prior art. This method, which allows the encapsulation of molecules in liquid or solid form, is based on the desolvation of macromolecules, leading to phase separation in solution.

With regard to encapsulation in lipid substances, a method of microencapsulation by thermal gelation is known. This method, known as melt deposition, is based on melting the coating material. The substance intended for encapsulation is dissolved or dispersed in the molten substance. The mixture is emulsified in a dispersing phase, the temperature of which is maintained above the melting temperature of the coating. Hardening of dispersed globules is achieved by quenching the medium.

Along with this type of microencapsulation of particles, molecular encapsulation (cyclodextrins) is also known. The latter is a preferred alternative to the standard encapsulation methods described above.

Actual cyclodextrins have been increasingly used for this purpose since the 1980s, as they are cell molecules capable of selectively and reversibly forming complexes with a wide range of organic molecules in the form of guest-host inclusion complexes. Cyclodextrin inclusion complexes are particularly useful for transporting, protecting and releasing chemically and thermally unstable ingredients. The release of complexed ingredients is usually carried out under the influence of water or temperature.

Cyclodextrins are a family of natural cyclic oligosaccharides obtained by enzymatic cleavage of starch. They consist of alpha-D-glucose units (from 6 to 12 units) linked to each other to form cycles defining a cavity having the shape of a truncated cone.

The most common are hexamers (α-cyclodextrin), heptamers (β-cyclodextrin), and octamers (γ-cyclodextrin), which differ in the number of glucose units and, accordingly, in the size of the conical cyclic cavity formed by them. All hydroxyl (OH) polar groups are located outside, giving the outer surface hydrophilicity, and explaining their solubility in water. Since the inner part of the cavity contains only glycosidic oxygen atoms and hydrogen atoms directly bonded by carbon atoms, this cavity is hydrophobic and much less polar. This amphiphilic nature gives cyclodextrins the ability to enclose lipophilic (hydrophobic) molecules in their cavity, provided that the size and geometric shape of these molecules allows them to form inclusion complexes that are usually soluble in water. Their non-toxic and biodegradable nature creates the prerequisites for their important applications in the food industry and pharmaceuticals. Encapsulation with cyclodextrins actually allows you to protect unstable molecules or to ensure their slow and controlled release. In addition, the solubilization of water-insoluble drugs in the form of cyclodextrin inclusion complexes allows you to get drugs for injection.

Natural cyclodextrins can be chemically modified, for example by producing ethers or esters that alter the solubility of both the modified cyclodextrins and inclusion complexes. This gives many advantages and allows the widespread use of cyclodextrins in various industries.

Cyclodextrins are also widely used as excipients in drugs. In particular, they make it possible to convert liquid compounds into solid ones (powders, tablets) by precipitating inclusion complexes. The complexation of the active ingredients makes it possible to better control their passage into the bloodstream or the process of their diffusion. Another application is sublingual treatment. Complexation of photosensitive or highly reactive ingredients often helps protect or stabilize them.

 In the food industry, cyclodextrins are also often used as flavor enhancers, making it easy to add flavoring compounds, or to fix too volatile molecules, and prolonging, for example, the duration of the taste of chewing gum. On the other hand, they are also used to remove certain undesirable molecules, in particular, to lower cholesterol or bitter substances in the finished food, or as masking agents against bad odors. Cyclodextrins are also used to stabilize emulsions such as mayonnaise or margarines.

In the cosmetics industry, they also stabilize emulsions and odorous or active substance molecules.

In the textile industry, they are used to connect active compounds (flavoring agents, bactericidal agents) with tissue.

However, commonly used cyclodextrins have disadvantages.

From a geometric point of view, inclusion will be determined by the relative size of the cyclodextrin cavity relative to the size of the guest molecule; if the indicated molecule is too large, it will not be able to penetrate the cyclodextrin cavity, or, on the other hand, if its size is too small, it will have few interactions with cyclodextrin. Therefore, the steric effect plays an important role in the phenomenon of complexation.

In addition, the molar ratio of cyclodextrin: guest molecule in the inclusion complex is usually 1: 1 or more, in other words, for the most part, one molecule is transferred to one cyclodextrin molecule.

Finally, the chemical nature of compounds capable of forming stable inclusion complexes with cyclodextrins is limited by lipophilic (hydrophobic) compounds, since they must replace water molecules in the cavity.

The relatively low solubility of cyclodextrins in water, in particular commercially available cyclodextrins, and in particular the most economically available cyclodextrin, β-cyclodextrin (18 g / l, i.e. 15 mmol / l at 25 ° C), may constitute a limitation for their use .

To remedy this situation, chemically modified cyclodextrins have been proposed in the prior art. For example, primary alcohols were replaced by monosaccharide or oligosaccharide groups, on the one hand, to increase their solubility in water, and on the other hand, to introduce cell recognition signals into their structure (international applications PCT WO 95/19994, WO 95/21870 and WO 97 / 33919).

However, derivatives of the cyclodextrins of the preceding region may have some limitations, in particular with respect to the substances that they are capable of transporting, their ability to form complexes with certain classes of molecules, in particular hydrophilic molecules, their cost, their toxicity, and the simplicity of their synthesis.

Cyclodextrin polymers are also known in the previous field, for which the stability constants of polymer-substrate complexes often exceed the stability constants of natural cyclodextrin-substrate complexes, and with which hydrophobic and hydrophilic compounds and supramolecules more readily form complexes and are more difficult to release by cyclodextrin polymers than in the case of natural cyclodextrins.

Thus, various types of cyclodextrin polymers and various preparation methods are known in the prior art (see, for example, Comprehensive Supramolecular Chemistry vol. 3, J.L. Atwood et al., Eds Pergamon Press (1996)).

These cyclodextrin polymers can be divided into two types depending on whether the cyclodextrin is the framework of this polymer or is a side substituent of the polymer chain.

The methods for synthesizing these cyclodextrin polymers of the preceding region in which cyclodextrin forms the framework are based on the use, as a rule, of difunctional crosslinking agents, such as epichlorohydrin, dialdehydes, diacids, diesters, diisocyanates, dihalogenated derivatives, polyisocyanates, bis-epoxides, dihalanides solvent, or phytic acid.

A method for producing copolymers of cyclodextrin (cyclodextrins) using epichlorohydrin has been proposed by Solms and Egi (Helv. Chim. Acta 48, 1225 (1965); US 3420788). Similarly, several modifications of the crosslinking method using epichlorohydrin were later proposed in Wiedenhof N. Et al., Die Starke 21 (5), 119-123 (1989). Hoffman J. L., J. Macromol. Sci.-Chem, A7 (5), 1147-1157 (1973), JP58171404 and JP61283601.

A method using a bifunctional agent such as dialdehyde, diacid, diester, dihalogen acid, diepoxide, diisocyanate, or dihalogenated derivative is described in US Pat. No. 3,472,835. This method discusses the activation of cyclodextrins by the action of sodium metal in aqueous liquid ammonia, and then differential crosslinking agent.

A method using polyisocyanates in aprotic organic solvents is described in US Pat. No. 4,917,956 to Asanuma H. et al. Chem. Commun, 1972-1972 (1997) and WO9822197.

A method using ethylene glycol bis (epoxypropyl) ester is described by Fenyvesi E. et al. in the Ann document. Univ. Sci. Budapest, Rolando Eotvos Nominatae, Sect. Chim. 15, 13-22 (1979). A method using other diepoxy compounds is also described by Sugiura I. et al. in the Bull document. Chem. Soc. Jpn., (62, 1643-1651 (1989)).

A method using dicarboxylic acid dihalohydrides was developed in US Pat. Nos. 4,958,015 and 4,902,788.

A method based on the use of phytic acid (polyphosphoric acid) for crosslinking cyclodextrin by heat treatment in vacuo is described in US Pat. No. 5,734,031.

The main disadvantage of the methods for crosslinking cyclodextrins with epichlorohydrin is the corrosive and toxic properties of this reagent. Methods based on the use of diepoxy compounds turned out to be toxic and have a high cost. For crosslinking of polyisocyanates and dihalogen anhydrides with acids, it is necessary to use organic solvents that are harmful to the environment and therefore cannot be used on an industrial scale.

The second type of polymer is a polymer in which the cyclodextrin is a side group of the polymer chain, it is obtained by grafting cyclodextrin (cyclodextrins) or a derivative (derivatives) of cyclodextrin to an existing polymer chain.

Thus, DE19520989 describes the grafting of cyclodextrins to polymers. In addition, cyclodextrins were also functionalized with aldehyde groups, and then grafted to chitosan by reductive amination; a similar reaction is described by Tomoya T. et al. in J. Polym. Sci., Part A: Polym. Chem. 36 (11), 1965-1968 (1998).

Such cyclodextrin-based polymers can also be synthesized by functionalizing said cyclodextrin with polymerizable functional groups such as acryloyl or methacryloyl. This functionalization is accompanied by the polymerization or copolymerization of these derivatives. Similar methods are described in DE4009825, Wimmer T. et al. at Minutes Int. Symp Cyclodextrines 6 ^th 106-109, (1992) Ed. Hedges AR ed. Santé Paris, and Harada A. et al. in Macromolecules 9 (5), 701-704 (1976).

Finally, the method using acrylates, acrylic acid and styrene with immobilization of cyclodextrin was carried out by emulsion polymerization in document EP780401.

To obtain polymers of cyclodextrin under non-polluting conditions, non-toxic and less expensive than the conditions of the above method, Martel et al described, in patent EP1165621B1, the synthesis of polymers from a solid mixture of cyclodextrin, polycarboxylic acid or polycarboxylic acid anhydride and a crosslinking catalyst, at a temperature of 100 to 200 ° C without the use of an organic solvent. The mechanical properties and molecular weight of these polymers are not regulated, while the latter have low stability and low molecular weight. In the work of Martel et al. (Journal of Applied Polymer Science, Vol. 97, 433-443 (2005)) describes a yield of 10% for the preparation of soluble polymers and 70% for the production of insoluble polymers. These yields are low and require a very long purification step (60 hours of dialysis) followed by lyophilization.

WO0148025 (Kimberly Klarck) discloses a method for preparing a composition comprising reacting cyclodextrin with a polysaccharide, for example cellulose fibers, by crosslinking with a reactive anionic polymer to form ester bonds between them. Reactive anionic polymer contains functional anionic groups in the form of cyclic anhydride, such as maleic acid anhydride, and can interact with the catalyst, in particular with sodium hypophosphite. The reactive anionic polymer used in these examples is BELCLENE DP80® maleic anhydride / vinyl acetate / ethyl acetate terpolymer (Durable Press 80). The resulting cyclodextrin polycondensate has a low ability to capture badly smelling compounds and has a weak ability to encapsulate a useful active ingredient like a fragrant.

Therefore, there remains a need to provide novel cyclodextrin polymers that are capable of capturing and / or encapsulating large amounts of substances without the drawbacks mentioned above, and which are readily prepared without the use of toxic and / or expensive reagents.

To overcome the disadvantages of the prior art, it is an object of the present invention to immobilize cyclodextrins in a crosslinked polymer network having absorbent properties and functioning as a sponge.

After conducting a significant study, it was surprisingly and unexpectedly found by the applicant that it is possible to efficiently, quickly and inexpensively immobilize cyclodextrins in a polymer crosslinked network by the esterification / polycondensation reaction of polycarboxylic acid (acids) simultaneously with a thermoplastic polyol polymer and cyclodextrin, and that the data are insoluble in water crosslinked cyclodextrin polycondensates lead to increased levels of efficiency with respect to encapsulating ability, while being portable to numerous substrates.

The results obtained form the basis of the present invention.

Thus, an object of the present invention is a water-insoluble cyclodextrin polycondensate, which can be obtained by an esterification / polycondensation reaction:

A) at least one cyclodextrin and

B) at least one saturated or unsaturated, or aromatic, linear or branched or cyclic polycarboxylic acid and / or at least one ester, one anhydride or one halide of said polycarboxylic acid, and

C) at least one thermoplastic polyol as one polymer and

D) optionally, in the presence of at least one esterification catalyst, and

E) optionally at least one cyclic polycarboxylic acid anhydride selected so that it is different from the polycarboxylic acid anhydride of paragraph B) and / or

F) optionally at least one non-polymeric polyol containing from 3 to 6 hydroxyl groups.

Another subject of this invention is the use of a cyclodextrin condensate, as previously defined, as an entraining agent.

The next subject of the invention relates, in particular, to the use of cyclodextrin condensate, as previously defined, as a capture agent for a substance or mixture of substances capable of polluting the environment, or a substance or mixture of substances capable of adversely affecting a consumer product.

A further subject of the invention relates, in particular, to the non-therapeutic cosmetic use of cyclodextrin condensate, as previously defined, as a capture agent for a substance or mixture of substances capable of leading, for example, to undesired reactions involving keratin substances, in particular human keratin substances.

A further subject of the invention relates, in particular, to the non-therapeutic cosmetic use of cyclodextrin condensate, as previously defined, as a capture agent for at least one useful active agent.

A further subject of the invention is a consumer product, comprising at least one cyclodextrin polycondensate as previously defined, and more specifically, the consumer product is a cosmetic or dermatological composition containing a physiologically acceptable medium.

Definitions

For the purposes of the invention, it is understood that the term "polycondensate" means any polymer that can be obtained by stepwise polymerization, where each stage is a condensation reaction that is carried out with the removal of water or alcohol, or a halogen-containing acid in the case of esterification. Monomers with two or more functional groups interact, forming first dimers, then trimers and longer oligomers, then long-chain polymers.

The term “water insoluble cyclodextrin polycondensate” is intended to mean any cyclodextrin polycondensate whose solubility in water at 25 ° C. is less than 1 mass%, even less than 0.5 mass%, or even less than 0.1 mass%.

For the purposes of the invention, the term “capture agent” is intended to mean any chemical compound, in particular any polymer capable of capturing a substance or mixture of substances into its structure, immobilizing it and / or slowing its release to the environment. Polymers based on the cyclodextrin polycondensate of the present invention have a porous network that combines superabsorbent bending properties with the ability to form inclusion complexes in the cavities of cyclodextrins immobilized inside the polymer network, thus allowing the capture of substances with affinity for the specified polymer network.

For the purposes of the present invention, it is understood that the term “physiologically acceptable medium” means an environment suitable for topical application of the composition.

The physiologically acceptable medium is preferably a cosmetically or dermatologically acceptable medium, that is, an environment devoid of unpleasant odor or appearance, and which is fully compatible with the local method of application.

The term "keratin materials" is intended to mean skin, skin, scalp, lips, and / or skin derivatives, such as nails and keratin fibers, such as animal skins, body hair, hair, eyelashes, eyebrows, and hair.

The term "human keratin materials" is intended to mean skin, scalp, lips, and / or skin derivatives, such as nails and human keratin fibers, such as body hair, eyelashes, eyebrows, and hair.

For the purposes of the invention, it is understood that the term “cosmetic composition” means any composition that has a non-therapeutic hygienic, caring, conditioning or makeup effect, which improves the appearance and / or makes it more attractive, or changes the appearance of the keratin suspension of a person to whom the composition is applied .

It is understood that “consumer product” means any manufactured product intended for use or consumption in the form in which it is sold and which is not intended for subsequent production or modification. Without limiting examples, the consumer products of the invention may be cosmetic formulations and adjuvants for use, or articles containing similar formulations, such as plasters, wipes, non-woven substrates, personal care products, including cosmetics and hygiene products, as well as intended for this purpose, such as sanitary tampons, napkins, towels, oral hygiene products such as toothpastes, oral care products, deodorants, such like sprays, lozenges for fresh breath, chewing gums, candies, cosmetic or dermatological products: creams, lotions, lotions, balms, pencils, powders, makeup products, hair products, products for babies, including formulations and products intended for this purposes, such as wipes, diapers, pharmaceuticals, and medical and paramedical products, such as dressings, plasters and prostheses, products for use in veterinary medicine, such as toilet fillers, hygiene products and / and whether for pet care, household chemical goods, such as detergents and / or detergents (detergents, softeners), dishwashing detergents, detergents for cleaning and / or maintaining home appliances, detergents and / or maintaining floors, tiles, wood, etc., hygiene products, such as deodorants, descalers, anti-stretch products, textile materials, clothing, leather goods, such as shoes, soles and support products They are in good condition, goods produced by the food industry, goods produced by the agricultural industry, phytosanitary products, goods produced by the woodworking and paper industries, paints, and ink.

For the purposes of the invention, it is understood that the term “beneficial agent” means any chemical compound present in a consumer product that has a beneficial effect noticed by the consumer during its use and / or obtained in the consumer product itself, while said beneficial effect may constitute a sensory improvement in particular, visual and / or olfactory and / or taste and / or tactile improvement, improvement or modification of convenience and / or ease of use, aesthetic impact ie, the hygienic effect, a feeling of cleanliness, therapeutic and / or prophylactic effect.

Cyclodextrin Polycondensates

Cyclodextrin polycondensates according to this invention can be easily obtained in one stage of synthesis and without the formation of waste, with low cost, in particular by conducting the reaction in an extruder.

In addition, it is possible to easily modify the structure and / or properties of the cyclodextrin polycondensates according to this invention by changing the chemical nature of its various components and / or proportions.

The cyclodextrin polycondensates according to this invention make it possible to obtain a porous polymer network that combines sponge-type superabsorbent properties with the ability to form inclusion complexes in the cavities of cyclodextrins immobilized within the polymer network.

Cyclodextrin polycondensates according to this invention can be obtained by esterification / polycondensation of the components described below by methods known to those skilled in the art.

Cyclodextrins

One of the components necessary to obtain cyclodextrin polycondensates according to this invention is cyclodextrin.

For the purposes of this invention, the term “cyclodextrin” is intended to mean any compound of general structure:

or a derivative thereof, such as methylated, hydroxyalkylated, sulfoalkylated or sulfated derivatives, or sugar substituted cyclodextrins.

Among the preferred cyclodextrins, α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin and their methylated derivatives, such as TRIMEBs (heptakis (2,3,6-trimethyl) -β-CD), DIMEBs (heptakis (2,6- dimethyl) -β-CD), or RAMEBs (randomly methylated β-cyclodextrins), their hydroxyalkylated derivatives, such as 2-hydroxypropyl-β-cyclodextrin (HPβCD, Kleptose® HPB), 3-hydroxypropyl-β-cyclodextrin, 2,3-dihydroxypropyl-β-cyclodextrin, 2-hydroxyethyl-β-cyclodextrin, 2-hydroxypropyl-γ-cyclodextrin and 2-hydroxyethyl-γ-cyclodextrin, sulfobutylated derivatives, such as β-cyclodextrin sulfobutyl ether sodium salt (SBEβCD, Captisol®), sulfated cyclodextrins, such as β-cyclodextrin sulfate, sugar-substituted cyclodextrins, glucosyl-β-cyclodextrin, diglucosyl-β-cyclodextrin, β-cyclodextrin, or dimaltosyl-β-cyclodextrin.

Of course, you can use a mixture of these cyclodextrins.

Preferably, the cyclodextrin is selected from α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin and mixtures thereof, but even best of all, β-cyclodextrin.

Cyclodextrin (s) preferably comprise (constitute) from 10% to 70% by weight, in particular from 20% to 65% by weight, and even better, from 30% to 60% by weight of the total mass used in the synthesis of cyclodextrin polycondensate.

Polycarboxylic acids and their derivatives

a) Polycarboxylic acids

The next component necessary to obtain the cyclodextrin polymers according to this invention is saturated or unsaturated, or aromatic, linear or branched, or cyclic polycarboxylic acid containing at least 2 carboxylic COOH groups, preferably from 2 to 4 COOH groups.

The specified polycarboxylic acid, in particular, can be selected from saturated or unsaturated, or even aromatic, linear, branched and / or cyclic polycarboxylic acids containing from 2 to 50 carbon atoms, in particular from 2 to 40, in particular from 3 to 36 carbon atoms, or even from 3 to 18, or even better, from 4 to 12 carbon atoms, or even from 4 to 10 carbon atoms, wherein said acid contains at least 2 carboxylic COOH groups, and preferably from 2 to 4 COOH groups.

In the range of polycarboxylic acids that can be used, it can be mentioned, separately, or in a mixture:

- dicarboxylic acids, such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecandioic acid, malic acid, tartaric acid, tartronic acid, citramalic acid, dioximealene , dioximalonic acid, maleic acid, fumaric acid, glutaconic acid, itaconic acid, fatty acid dimers (particularly C ₃₆ fatty acids), such as products sold under the name Pripol 1006, 1009, 1013 and 1017 by Uniqema, glutamic acid, aspartic acid, oxaloacetic acid, cyclopropane dicarboxylic acid, cyclohexanedicarboxylic acid, cyclobutanedicarboxylic acid, naphthalene-1,4-dicarboxylic acid, naphthalene-2,3-dicarboxylic acid 2,6-dicarboxylic acid, phthalic acid, terephthalic acid, isophthalic acid, tetrahydrophthalic acid, or hexahydrophthalic acid,

- tricarboxylic acids, such as citric acid, aconitinic acid, isolimonic acid, oxalosuccinic acid, 1,2,3-propanetricarboxylic acid, 1,2,5-pentantricarboxylic acid, 1,3,5-pentantricarboxylic acid, trans-aconitinic acid, 3-butene-1,2,3-tricarboxylic acid, 3-butene-1,1,3-tricarboxylic acid, 1,3,5-cyclohexanetricarboxylic acid, trimellitic acid, 1,2,3-benzenetricarboxylic acid or 1,3 5-benzenetricarboxylic acid,

- tetracarboxylic acids, such as 1,2,3,4-butanetetracarboxylic acid, pyromellitic acid, hydroxy succinic acid, thio di succinic acid, N- [1,2-dicarboxyethyl] -L-aspartic acid, ethylenediaminetetraacetic acid, ethylenediaminetetrapropionic acid, or N, N'-ethylenedi (L-aspartic) acid.

Preferably, said polycarboxylic acid, used individually or as a mixture, is aliphatic, saturated and linear, and contains from 2 to 36 carbon atoms, in particular from 3 to 18 carbon atoms, or even from 4 to 12 carbon atoms, or, alternatively, is aromatic, and contains from 8 to 12 carbon atoms. Preferably, it contains from 2 to 4 COOH groups.

Preferably, citric acid, aconitinic acid, tartaric acid, 1,2,3-propanetricarboxylic acid, and 1,2,3,4-butanetetracarboxylic acid can be used, individually or as a mixture, preferably individually, and even better, individually citric acid.

b) Polycarboxylic esters

Among the ester derivatives of polycarboxylic acids, mention may be made of C ₁ -C ₄ alkyl mono-, di-, tri- or tetraesters, in particular methyl, ethyl, isopropyl or n-butyl esters, and more preferably methyl or ethyl esters.

Preferred polycarboxylic acid esters are methyl, ethyl, isopropyl or n-butyl esters, and more preferably methyl or ethyl esters of aliphatic, saturated, linear polyacids (from 2 to 4 COOH groups) containing from 2 to 36 carbon atoms, in particular from 3 to 18 carbon atoms, or even from 4 to 12 carbon atoms, or, alternatively, or alternatively, an aromatic acid containing from 8 to 12 carbon atoms. Preferably, methyl, ethyl, isopropyl or n-butyl esters can be used, and even more preferably ethyl or butyl esters of citric acid, aconitinic acid, tartaric acid, 1,2,3-propanetricarboxylic acid and 1,2,3,4- butane tetracarboxylic acid, individually or as a mixture, ethyl or butyl citric acid esters such as triethyl citrate, acetyl triethyl citrate, tributyl citrate and acetyl tributyl citrate are even better.

c) Polycarboxylic Acid Anhydrides

Among the anhydrides obtained from polycarboxylic acids, mention may be made of:

a) mixed anhydrides of C ₂ -C ₄ carboxylic acid, in particular acetic acid, propionic acid or butyric acid, preferably acetic acid;

b) cyclic polycarboxylic acid anhydrides such as phthalic anhydride, trimillite anhydride, maleic anhydride, succinic anhydride or N, N, N ’, N’-ethylenediaminetetraacetic acid dianhydride.

Preferably, the polycarboxylic acid anhydride, individually or as a mixture, is selected from maleic anhydride and succinic anhydride, and more preferably, it is an individual maleic anhydride.

d) Polycarboxylic Acid Halides

Among the halides obtained from said polycarboxylic acids, mention may be made of acid chlorides or bromides of said polycarboxylic acids, preferably polycarboxylic acid chlorides.

Preferably, the halides used individually or as a mixture are the halides of aconitinic acid, tartaric acid, 1,2,3-propanetricarboxylic acid or 1,2,3,4-butanetetracarboxylic acid, and preferably the acid chlorides.

The specified polycarboxylic acid (s) and / or its ester, acid anhydride or derivatives of acid anhydride, used individually or as a mixture, preferably comprises (constitute) from 5% to 40 mass%, more preferably from 7% to 35 mass% and even better, from 10% to 30 mass%, based on the total mass used in the synthesis of cyclodextrin polycondensate.

Thermoplastic Polyol Polymers

Another component necessary to obtain a cyclodextrin condensate according to the present invention is a thermoplastic polyol polymer.

The term "polyol polymer" is intended to mean a polymer with an average molecular weight of from 1,000 to 200,000 daltons containing at least two hydroxyl functional groups.

It is understood that the term "thermoplastic polyol as one polymer" means a polymer that liquefies (softens) when heated to a temperature of from 100 to 250 ° C.

Various types of thermoplastic polyol polymers can be used in accordance with the invention. Mention may be made of polyether ethers-polyols, polyesters-polyols, polyamides-polyols, polyurethane-polyols, polyalkylene-polyols, polycaprolactone-polyols and polysaccharides.

Among the polyether ether polyols, mention may be made of polyoxyethylene glycols, polyoxypropylene glycols, block or random copolymers of ethylene oxide and / or propylene oxide with tetrahydrofuran, and more particularly polytetramethylene glycols and polypropylene glycols.

Among the polyester esters-polyols, mention may in particular be made of polyester esters-polyols which can be obtained by polycondensation of dicarboxylic or tricarboxylic acids with polyols (di-, tri- or tetraols), for example poly (hexamethylene adipate), and poly esters are polyols which can be obtained by polycondensation of hydroxy acids, such as polyhydroxyalkanoates and, in particular, polylactic acid, polyhydroxybutyrate (PHB) and polyhydroxybutyrate valerate (PHBV).

Among the polycarbonate polyols, mention may be made of polycarbonate polyols, which can be obtained by reacting diols (propane-1,3-diol, butane-1,4-diol, hexane-16-diol, 1,9-nonanediol, 2-methyl-octane-1 , 8-diol, diethylene glycol and so on) with diaryl carbonates, such as diphenyl carbonate, or with phosgene.

Among the polyamide polyols, mention may be made more particularly of polyamide polyols, which can be obtained by reacting a diamine and / or a polymer diamine with a dicarboxylic or polycarboxylic acid and a hydroxy acid, for example, such as 12-hydroxystearic acid.

Among the polyurethane-polyols, mention may be made of polyurethane-polyols, which can be obtained by the coupling method of reacting polyisocyanates, preferably diisocyanates, with diols and / or polyols.

Among the polycaprolactone polyols, mention may in particular be made of polycaprolactone polyols, which can be obtained by polymerization of exilon-caprolactone with ring opening by polyols such as ethylene glycol, 1,2-propanediol, 1,3-propanediol, glycerol or trimethylolpropane.

In the series of polyalkylene-polyols, mention may be made of polyvinyl alcohol, modified polyvinyl alcohol with an ethylene content of 4 mol% to 15 mol%, and polybutadiene diols.

Among the polysaccharides, it is possible to mention specifically thermoplastic starches, which are obtained by the degradation of a natural granule in the presence of a plasticizer under thermomechanical pressure, cellulose derivatives such as cellulose acetate, cellulose acetate butyrate, cellulose acetate, hydroxyethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl cellulose, hydroxypropyl cellulose, hydroxypropyl cellulose, hydroxyethyl cellulose, cellulose, hydroxyethyl cellulose, cellulose, hydroxyethyl cellulose, individually or as a mixture with alginates, resins, and as guar gum, starches such as tapioca starch, modified starches such as starch octenyl succinate (E.1450), oxidized starches (E.1404), crosslinked starches (E.1412 or 1413), stabilized starches (E.1420 or E.1440), crosslinked / stabilized starches such as acetylated dicarch starch adipate (E.1422) or hydroxypropylated starch phosphate (E.1442), sulfated polysaccharides such as carrageenans, aminopolysaccharides such as chitosan or quinine, such as oxidized polysaccharides such as oxidized polysaccharides described as disclosed in WO 2010/070235, patent FR2944967 and WO 2011/161020, and more specifically, starches, inulin, carrageenans, alginates and glucomannans.

Polysaccharides are particularly preferred as they are a renewable natural resource and are available in large quantities and at low cost.

Preferably, of the polysaccharides, hydroxypropyl cellulose and hydroxyethyl cellulose, and even better, only hydroxypropyl cellulose can be used, individually or as a mixture.

The specified thermoplastic polyol polymer (s) preferably constitutes (make up) from 10% to 50 mass%, in particular from 15% to 45 mass%, and even better, from 17% to 40 mass% of the total mass used in the synthesis of cyclodextrin polycondensate.

Polycarboxylic Acid Cyclic Anhydrides

According to one particular form of the present invention, at least one cyclic polycarboxylic acid anhydride, selected so that it differs from the previously mentioned first polycarboxylic acid anhydride, is also used to produce cyclodextrin polycondensates according to this invention.

The additional cyclic polycarboxylic acid anhydride may, in particular, correspond to one of the following formulas:

in which groups A and B are, independently of each other:

- a hydrogen atom,

a saturated or unsaturated, linear, branched and / or cyclic, or alternatively, carbon-based aromatic radical containing from 1 to 16 carbon atoms, in particular from 2 to 10 carbon atoms, or even from 4 to 6 carbon atoms in particular methyl or ethyl,

- or, alternatively, A and B together form a saturated or unsaturated, or even an aromatic ring containing a total of 5 to 7, and in particular 6 carbon atoms.

Preferably, A and B represent a hydrogen atom or together form an aromatic ring containing a total of 6 carbon atoms.

Among the cyclic polycarboxylic acid anhydrides that can be used, mention may be made, individually or as a mixture, of phthalic anhydride, trimellitic anhydride, maleic anhydride and succinic anhydride.

Preferably, maleic anhydride and succinic anhydride can be used, individually or as a mixture, or, even better, only maleic anhydride.

When said cyclic polycarboxylic acid anhydride is present among the ingredients used, it is preferably from 0.1% to 10 mass%, in particular from 0.5% to 5 mass%, or even from 0.7% to 4 mass%, relative to the total mass used in the synthesis of cyclodextrin polycondensate.

Esterification catalysts

According to one particular form of the invention, at least one esterification catalyst will be used to prepare the cyclodextrin polycondensates of the invention.

In particular, the esterification catalyst can be selected from dihydrogen phosphates, hydrophosphates, phosphates, hypophosphites and phosphites of alkali metals, alkali metal salts with polyphosphoric acids, carbonates, hydrocarbons, acetates, borates and hydroxides of alkali metals or alkaline earth metals, amines and aqueous ammonia, optionally in the compound with an inorganic solid support such as alumina, silica gels, Al silicates, zeolites, titanium oxides or zirconium oxides. The esterification catalyst can also be selected from sulfonic acids or titanates.

Preferably, sodium hydrogen phosphate, sodium dihydrogen phosphate and sodium hypophosphite, and even better sodium dihydrogen phosphate, can be used.

In the presence of said esterification catalyst among the ingredients used, it is preferably from 0.1% to 5 mass%, in particular from 0.5% to 4 mass%, or even from 0.5% to 3 mass% relative to the total mass used in the synthesis of cyclodextrin polycondensate.

Nonpolymer Polyols

According to one particular form of the present invention, at least one non-polymeric polyol containing from 3 to 6 hydroxyl groups will be used to prepare the cyclodextrin polycondensates of the present invention. Of course, you can also use a mixture of such polyols.

The specified polyol, in particular, can be a linear, branched and / or cyclic, saturated or unsaturated carbon or, in particular, hydrocarbon compound containing from 3 to 18 carbon atoms, in particular from 3 to 12, or even from 4 to 10 carbon atoms, and from 3 to 6 hydroxyl (OH) groups, and possibly also containing one or more oxygen atoms introduced into the chain (ether functional group).

The specified polyol is preferably a linear or branched saturated hydrocarbon compound containing from 3 to 18 carbon atoms, in particular from 3 to 12, or even from 4 to 10 carbon atoms, and from 3 to 6 hydroxyl (OH) groups.

It can be selected, individually, or as a mixture, from:

- triols, such as 1,2,4-butanetriol, 1,2,6-hexanetriol, trimethylol ethane, trimethylol propane or glycerin,

- tetraols, such as pentaerythritol (tetramethylolmethane), erythritol, diglycerin or dithrimethylolpropane,

- pentols, such as xylitol,

- hexols, such as sorbitol and mannitol, or, alternatively, dipentaerythritol or triglycerin.

Preferably, the polyol is selected from glycerol, pentaerythritol, diglycerol and sorbitol, and mixtures thereof, and even better, the polyol is only glycerol.

In the case where the specified polyol containing from 3 to 6 hydroxyl groups is among the ingredients used, it is preferably from 1% to 30 mass%, in particular from 2% to 25 mass%, or even from 10% to 20 mass% relative to the total mass used in the synthesis of cyclodextrin polycondensate.

In one of the preferred embodiments of the present invention, the ratio of the number of moles of polycarboxylic acid to the number of moles of cyclodextrin preferably ranges from 0.5 to 5, in particular from 0.6 to 4, and in particular from 0.7 to 3.

It was noted that these ratios make it possible to obtain cyclodextrin polycondensate, which is preferably insoluble in water and which, moreover, has at the same time the corresponding ability to capture and impregnation with various ingredients.

Preferably, the cyclodextrin polycondensate according to this invention has an acid number, expressed in mg of potassium hydroxide per g of polycondensate, greater than or equal to 20, in particular in the range of 20 to 250, and even better in the range of 40 to 180.

One of skill in the art can readily determine the acid number by standard analytical methods. The amount of α-COOH groups present is estimated by the number of milligrams of potassium hydroxide necessary to neutralize 1 g of cyclodextrin polycondensate, while the dispersion is carried out in a solvent mixture (1 g of water and 1 g of absolute ethanol).

Preferably, the cyclodextrin polycondensate according to this invention exhibits a degree of swelling in water, determined at 20 ° C, which is greater than or equal to 100%, in particular, is in the range from 100% to 1000%, and even better, is in the range from 300% to 900% The degree of swelling is determined by the method described below.

Protocol for determining the degree of swelling

2 g of polycondensate are suspended in 20 g of demineralized water with gentle stirring for 24 hours at ambient temperature. The suspension is centrifuged to separate the supernatant, and then the solids in the centrifuge are determined using heat balance. % The degree of swelling is obtained by calculating the ratio of the evaporated mass / dry matter mass × 100.

The polycondensate according to this invention can be obtained by the methods of esterification / polycondensation, which are usually used by specialists in this field.

By way of illustration, a general method of preparation includes:

- mixing one or more cyclodextrins, a polycarboxylic acid and / or its derivative (esters, acid anhydrides or acid halides) of at least one thermoplastic polyol polymer and, optionally, at least one cyclic polycarboxylic acid anhydride thus selected so that it differs from the previous polycarboxylic acid anhydride and / or at least one esterification catalyst and / or at least one non-polymeric polyol containing from 3 to 6 hydroxyl ial groups,

- heating the mixture, preferably in an inert atmosphere, to a temperature in the range from 100 to 250 ° C, preferably while removing the generated water, alcohol or acid when heated, then

- cooling the mixture to ambient temperature.

You can also carry out this reaction, in whole or in part, in an inert solvent, such as xylene and / or under reduced pressure, to facilitate the removal of the resulting water, alcohol or acid.

Preferably, no solvent is used.

The specified method of obtaining may also include the stage of adding to the reaction mixture at least one oxidation inhibitor, in particular, in a mass concentration, preferably in the range from 0.01% to 2%, relative to the total mass used in the synthesis of cyclodextrin polycondensate to limit possible decomposition associated with prolonged heating.

This oxidation inhibitor can be selected from sterically hindered phenols, aromatic secondary amines, organophosphorus compounds, sulfur compounds, lactones and bisphenols, and mixtures thereof.

Among the particularly preferred oxidation inhibitors, in particular, mention may be made of BHT, BHA, TBHQ, 1,3,5-trimethyl-2,4,6-tris (3,5-di (tert-butyl) -4-hydroxybenzyl) benzene, octadecyl 3,5-di (tert-butyl) -4-hydroxycinnamate, tetrakis [methylene-3- (3,5-di (tert-butyl) -4-hydroxyphenyl) propionate] methane, octadecyl 3- (3,5-di (tert-butyl) - 4-hydroxyphenyl) propionate, 2,5-di (tert-butyl) hydroquinone, 2,2- (hydroxyphenyl) propionate, 2,5-di (tert-butyl) hydroquinone, 2,2-methylenebis (4-methyl-6- (tert-butyl) phenol), 2,2-methylenebis (4-ethyl-6- (tert-butyl) phenol), 4,4-yutylidenebis (6- (tert-butyl) -m-cresol), N, N-hexamethylene c (3,5-di (tert-butyl) -4-hydroxyhydrocinnamide), pentaerythritol tetrakis (3- (3,5-di (tert-butyl) -4-hydroxyphenyl) propionate), in particular a product sold by Ciba under the name Irganox 1010, octadecyl 3- (3,5-di (tert-butyl) -4-hydroxyphenyl) propionate, in particular a product sold by Ciba under the name Irganox 1076, 1,3,5-tris (3,5-di (tert-butyl) -4- hydroxybenzyl) -1,3,5-triazine-2,4,6 (1H, 3H, 5H) -trione, in particular the product sold by Mayzo of Norcross, Ga, under the name BNX 3114, di (stearyl) pentaerythritol diphosphite, tris (2,4-di (tert-butyl) phenyl) phosphite, in particular a product sold by Ciba under the name Irganox 1 68, dilauryl thiodipropionate, in particular a product sold by Ciba under the name Irganox PS800, bis (2,4-di (tert-butyl) pentaerythritol) diphosphite, in particular a product sold by Ciba under the name Irgafos 126, bis (2,4-bis ) [2-phenylpropan-2-yl] phenyl) pentaerythritol diphosphite, triphenylphosphite, (2,4-di (tert-butyl) phenyl) pentaerythritol diphosphite, in particular the product sold by Ciba under the name Ultranox 626, tris (nonylphenyl) phosphite, in particular product sold by Ciba under the name Irgafos TNPP, a 1: 1 N mixture, N-hexamethylene bis (3,5-di (tert-butyl) -4-hydroxyhydrocinnamide) and tris (2,4-di (tert-butyl) phenyl) osfate, in particular a product sold by Ciba under the name Irganox B 1171, tetrakis (2,4-di (tert-butyl) phenyl) phosphite, in particular a product sold by Ciba under the name Irgafos P-EPQ, distearyl thiodipropionate, in particular a product Ciba under the name Irganox PS802, 2,4-bis (octylthiomethyl) -o-cresol, in particular a product sold in Ciba under the name Irganox 1520, 4,6-bis (dodecylthiomethyl) -o-cresol, in particular sold by Ciba under the name Irganox 1726.

One particularly preferred embodiment for preparing the cyclodextrin polycondensates of the present invention is to mix at least one cyclodextrin, at least one polycarboxylic acid and / or its derivative of an ester, acid anhydride or acid halide, at least one thermoplastic polyol polymer and optionally at least one cyclic polycarboxylic anhydride selected so that it differs from the previous polycarboxylic anhydride acid, and / or at least one esterification catalyst, and / or at least one non-polymeric polyol in the installation, which allows you to bring this mixture to a thermoplastic state by combining the conditions of sufficient temperature and shear stress, thus leading , to the compatibility of various components.

Preferably, an extruder is used, for example, Clextral BC 21® twin screw type, or any other installation that meets these criteria, which operates at a temperature of from 100 to 250 ° C, and preferably from 110 to 200 ° C.

A preferred embodiment for preparing the materials of this invention consists in introducing, in one step, all the ingredients into an extruder at a temperature of from 110 to 200 ° C, preferably from 120 to 190 ° C, and even better, from 150 to 180 ° C.

The residence time in the extruder preferably varies from 1 to 10 minutes, and even better, from 1 to 5 minutes.

Depending on the intended use of the cyclodextrin polycondensate of the present invention, if necessary, said polycondensate can then be ground.

Another subject of this invention is the use of a cyclodextrin polycondensate, as previously defined, as a means of trapping a substance or mixture of substances that can pollute the environment, such as gaseous pollutants (volatile organic compounds), metal cations, oils and fats, pollutants in drinking water, industrial water and aqueous wastewater, as well as in soils and surrounding volatile molecules of odorous substances.

Among the gaseous pollutants (VOCs), mention may in particular be made of chlorine compounds, for example chlorobenzene, carbon tetrachloride and monovinyl chloride.

Among the metal cations, in particular, cations of lead, cadmium, mercury, iron and copper can be mentioned.

Oils and fats are of mineral, animal, vegetable, marine or synthetic origin. Of these, complex mixtures of hydrocarbon oils constituting fuels, lubricants and hydraulic fluids, as well as additives added in small quantities to improve technical characteristics, for example, antiknock agents, oxidation inhibitors, antifreezes, lead substitutes and dyes, can be mentioned.

Of the pollutants contained in drinking water, industrial water and aqueous wastewater, in particular, fetid natural pollutants of drinking water can be mentioned, for example, (-) - geosmin and (+) - 2-methylisobornoleol.

Of the pollutants contained in the soils, chlorophenols (tri- and pertachlorophenol) and polycyclic aromatic hydrocarbons (naphthalene, phenanthrene) can be specifically mentioned.

The cyclodextrin polycondensate of the present invention, due to its chemical nature and its superabsorbent polymer network, has, in particular, a strong ability to absorb fatty substances, such as vegetable oils, mineral oils, for example, hydrocarbons such as isohexadecane, paraffin oil, terpenes, squalene, isoparaffins, ceresin, petroleum jelly, hydrogenated oils, silicone oils, saturated or unsaturated fatty acids (such as oleic acid), fatty acid esters, fatty alcohols (such as myristyl alcohol, cetyl alcohol, stearyl alcohol, myricyl alcohol), buffering agents, ester waxes, or mixtures thereof.

Cyclodextrin polycondensates allow, in particular, to capture fats, dirt, fatty waste resulting from the production or consumption of numerous consumer products, in particular food products, household goods, for example, washing powders, cleaning products for fabrics, for example, stain removers, products for cleaning and / or keeping floors in good condition, cosmetic cleansers, such as makeup removers.

Another subject of this invention is the use of a cyclodextrin polycondensate, as previously defined, as a means for trapping and protecting a substance or mixture of substances that can decompose under the influence of atmospheric factors (moisture, heat, oxygen, light, etc.) or in contact with one or more ingredients composition.

Of these substances, which are called particularly sensitive, easily degradable or unstable, in particular, fragrant substances (perfume ingredients) and fragrances, vitamins, hormones and dyes can be mentioned.

The next subject of this invention is the non-therapeutic cosmetic use of cyclodextrin polycondensate, as previously defined, as a means for capturing a substance or mixture of substances that can lead, for example, to the occurrence of undesired reactions involving keratin substances and, in particular, human keratin substances.

Substances that can lead to the occurrence of undesirable reactions involving keratinous substances, in particular human keratinic substances, in particular, are selected from:

fetid substances, in particular molecules of foul-smelling physiological fluids,

components of human sweat,

sebum components.

Among the substances that can cause discomfort with respect to keratinous substances and, in particular, human keratinous substances, we can mention molecules of malodorous substances and, in particular, molecules of foul-smelling physiological fluids formed by sweat and bacteria that multiply in it during its formation.

Among the molecules of foul-smelling physiological fluids, we can mention:

a) linear or branched, saturated or unsaturated and / or optionally substituted C ₂ -C ₂₀ fatty acids, such as acids of the following formula (1):

R ₁ -C (O) -OH (1)

in which R ₁ represents i) a linear or branched (C ₁ -C ₂₀ ) alkyl group, which is optionally substituted, preferably by at least one hydroxyl group,

ii) a linear or branched (C ₂ -C ₂₀ ) alkenyl group which is optionally substituted with at least one hydroxyl group, in particular this alkyl or alkenyl group contains from 2 to 14 carbon atoms.

Among the molecules of foul-smelling physiological fluids, mention may in particular be made of acetic acid, 2-propenoic acid, propanoic acid, propionic acid, 2-methylpropanoic acid, 2-methylpropenoic acid, 2-butenoic acid, 2-methyl-2-butenoic acid , 3-methyl-2-butenoic acid, butanoic acid, 2-methylbutanoic acid, 3-methylbutanoic acid, 3-hydroxybutanoic acid, 3-hydroxy-3-methylbutanoic acid, 2-methylbutyric acid, isovaleric acid, 2-pentenoic acid, 2-methyl-2-pentenoic acid, 3-methyl-2-pente hydrochloric acid, pentanoic acid, 2-methylpentanoic acid, 3-methylpentanoic acid, 3-hydroxypentanoic acid, 3-hydroxy-3-methylpentanoic acid, 3-methylhexanoic acid, 3-hydroxy-3-methylhexanoic acid, hexanoic acid, (E) -3-methyl-2-hexenoic acid, 2-heptenoic acid, 2-methyl-2-heptenoic acid, 3-methyl-2-heptenoic acid, heptanoic acid, 2-methylheptanoic acid, 3-methylheptanoic acid, 3-hydroxyheptanoic acid , 3-hydroxy-3-methylheptanoic acid, octanoic acid, 2-methyloctanoic acid, 3-methyloctane hydrochloric acid, 3-hydroxyoctanoic acid, 3-hydroxy-3-methyl-octanoic acid, nonanoic acid, 2-nonenoic acid, 2-methyl-2-nonenoic acid, 3-methyl-2-nonenoic acid, nonanoic acid, 2-methylnonanoic acid , 3-methylnonanoic acid, 3-hydroxynonanoic acid, 3-hydroxy-3-methylnonanoic acid, 2-decenoic acid, 2-methyl-2-decenoic acid, 3-methyl-2-decenoic acid, decanoic acid, 2-methyldecanoic acid , 3-methyldecanoic acid, 3-hydroxydecanoic acid, 3-hydroxy-3-methyldecanoic acid, 10-hydroxydecanoic acid , 2-undecenoic acid, 2-methyl-2-undecenoic acid, 3-methyl-2-undecenoic acid, undecanoic acid, 2-methylundecanoic acid, 3-methylundecanoic acid, 3-hydroxyundecanoic acid, 3-hydroxy-3-methylundecanoic acid , dodecanoic acid, 2-hydroxy-dodecanoic acid, tridecanoic acid, 2-hydroxy-dodecanoic acid and tridecanoic acid.

In particular, aromatic fatty acids are selected from propionic acid, 3-methyl-2-hexenoic acid, isovalerianic acid, 2-methylbutyric acid, hexanoic acid, octanoic acid, nonanoic acid, decanoic acid and dodecanoic acid.

b) mercaptoalkanols, such as mercaptoalkanols of the following formula (2):

HS-R ₂ -OH (2)

in which R ₂ represents a linear or branched (C ₁ -C ₁₀ ), and preferably, (C ₁ -C ₆ ) alkylene group.

In particular, the aromatic molecules of mercaptoalkanols are selected from 3-methyl-3-sulfanylhexan-1-ol, 3-sulfanylhexan-1-ol, 2-methyl-3-sulfanylbutan-1-ol, 3-sulfanylpentan-1-ol, 3- sulfanylbutan-1-ol, 3-methyl-3-sulfanylpentan-1-ol and 3-methyl-3-sulfanylbutan-1-ol,

c) steroids such as steroids selected from androst-16-ene steroids, in particular 5α-androst-16-en-3-one and 5α-androst-16-en-3α-one, androst-2-en- 17-on, androst-4,16-dien-3-one, androst-5,16-dien-3-ol, androst-4-en-3,17-dione, androstan-3-one, DHEA (dehydroepiandrosterone) , testosterone, DHT (dehydrotestosterone) and 3-hydroxy-5-androstan-17-one,

d) sulfoconjugate steroids, in particular sulfate derivatives of the compounds defined in paragraph c) above.

In particular, aromatic sulfoconjugate steroid compounds are preferably selected from sulfates derived from dehydroepiandrosterone (DHEA), from androsterone and from testosterone, 5α-androst-16-ene-3α-sulfate, androst-5,16-diene-3β-sulfate, sulfate dehydroepiandrosterone, testosterone sulfate and 5α-androstan-17-one-3α-sulfate,

e) fragrance precursors are selected from conjugated fatty amino acids, such as the conjugated product of glutamine with (E) -3-methyl-2-hexenoic acid (a) and the conjugated product of glutamine with 3-hydroxy-3-methylhexanoic acid (b).

The following compounds may also be mentioned:

N2- [3-methylhex-2-enoyl] glutamine, N2- [3-methyl-3-hydroxyhexanoyl] glutamine, N2-acetylglutamine, N2- [prop-2-enoyl] glutamine, N2- [2-methylprop-2- enoyl] glutamine, N2-propanoylglutamine, N2- [2-methylpropanoyl] glutamine, N2- [but-2-enoyl] glutamine, N2- [2-methylbut-2-enoyl] glutamine, N2-butanoylglutamine, N2- [2- methylbutanoyl] glutamine, N2- [3-methylbutanoyl] glutamine, N2- [3-hydroxybutanoyl] glutamine, N2- [3-hydroxy-3-methylbutanoyl] glutamine, N2- [pent-2-enoyl] glutamine, N2- [2 -methylpent-2-enoyl] glutamine, N2-pentanoylglutamine, N2- [2-methylpentanoyl] glutamine, N2- [3-methylpentanoyl] glutamine, N2- [3-hydroxypentanoyl ] glutamine, N2- [3-hydroxy-3-methylpentanoyl] glutamine, N2- [hex-2-enoyl] glutamine, N2- [2-methylhex-2-enoyl] glutamine, N2-hexanoylglutamine, N2- [2-methylhexanoyl ] glutamine, N2- [3-methylhexanoyl] glutamine, N2- [3-hydroxyhexanoyl] glutamine, N2- [hept-2-enoyl] glutamine, N2- [2-methylhept-2-enoyl] glutamine, N2-heptanoylglutamine, N2 - [2-methylheptanoyl] glutamine, N2- [3-methylheptanoyl] glutamine, N2- [3-hydroxyheptanoyl] glutamine, N2- [3-hydroxy-3-methylheptanoyl] glutamine, N2- [oct-2-enoyl] glutamine, N2- [2-methylloct-2-enoyl] glutamine, N2-octanoyl glutamine, N2- [2-methyl-octanoyl] glutamine, N2- [3-methyl-octanoyl] glutam in, N2- [3-hydroxyoctanoyl] glutamine, N2- [3-hydroxy-3-methyloctanoyl] glutamine, N2- [non-2-enoyl] glutamine, N2- [2-methylnon-2-enoyl] glutamine, N2- nonanoyl glutamine, N2- [2-methylnonanoyl] glutamine, N2- [3-methylnonanoyl] glutamine, N2- [3-hydroxynonanoyl] glutamine, N2- [3-methylnonanoyl] glutamine, N2- [3-hydroxynonanoyl] glutamine, N2 3-hydroxy-3-methylnonanoyl] glutamine, N2- [dec-2-enoyl] glutamine, N2- [2-methyldec-2-enoyl] glutamine, N2-decanoylglutamine, N2- [2-methyldecanoyl] glutamine, N2- [ 3-methyldecanoyl] glutamine, N2- [3-hydroxydecanoyl] glutamine, N2- [3-hydroxy-3-methyldecanoyl] glutamine, N2- [undec-2-enoyl] glu amine, N2- [2-methylundec-2-enoyl] glutamine, N2- [undkanoyl] glutamine, N2- [2-methyldundanoyl] glutamine, N2- [3-methylundecanoyl] glutamine, N2- [3-hydroxyundanoyl] glutamine, N2 - [3-hydroxy-3-methylundanoyl] glutamine, N2- [dodec-2-enoyl] glutamine, N2- [2-methyldodec-2-enoyl] glutamine, N2-dodecanoylglutamine, N2-2-methyldodecanoylglutamine, N2- [3 -methyldodecanoyl] glutamine, N2- [3-hydroxydodecanoyl] glutamine, N2- [3-hydroxy-3-methyldodecanoyl] glutamine and Nα-hexanoylglutamine,

f) fatty acid esters, such as esters of an acid of formula (1) as previously defined, preferably esters of the following formula (3):

R ₁ -C (O) -OR ' ₁ (3)

wherein:

R ₁ as previously defined, and

R ′ ₁ represents i) a linear or branched (C ₁ -C ₂₀ ) alkyl group which is optionally substituted with at least one hydroxyl group, ii) a linear or branched (C ₂ -C ₂₀ ) alkenyl group, which optionally substituted, preferably with at least one hydroxyl group.

According to one specific form, R ′ ₁ contains from 1 to 14 carbon atoms, and more specifically, R ′ ₁ represents a linear or branched (C ₁ -C ₆ ) alkyl group, such as methyl.

In particular, mention may be made of linear or branched (C ₁ -C ₆ ) alkyl esters, and in particular 3-hydroxy-3-methylhexanoic acid methyl ester, 3-hydroxy-4-methyl-octanoic acid, (E) -3-methyl -2-hexenoic acid, 3-hydroxyhexanoic acid and 3-hydroxyoctanoic acid.

You can also mention linear or branched (C ₁ -C ₆ ) alkyl esters and, in particular, methyl esters of the following acids:

acetic acid, 2-propenoic acid, propanoic acid, 2-methylpropanoic acid, 2-methylpropenoic acid, 2-butenoic acid, 2-methyl-2-butenoic acid, 3-methyl-2-butenoic acid, butanoic acid, 2-methylbutanoic acids, 3-methylbutanoic acid, 3-hydroxybutanoic acid, 3-hydroxy-3-methylbutanoic acid, 2-pentenoic acid, 2-methyl-2-pentenoic acid, 3-methyl-2-pentenoic acid, pentanoic acid, 2-methylpentanoic acids, 3-methylpentanoic acid, 3-hydroxypentanoic acid, 3-hydroxy-3-methylpentanoic acid, 2-he tenoic acid, 2-methyl-2-heptenoic acid, 3-methyl-2-heptenoic acid, heptanoic acid, 2-methylheptanoic acid, 3-methylheptanoic acid, 3-hydroxyheptanoic acid, 3-hydroxy-3-methylheptanoic acid, 2- octenoic acid, 2-methyl-2-octenoic acid, 3-methyl-2-octenoic acid, octanoic acid, 2-methyl-octanoic acid, 3-methyl-octanoic acid, 3-hydroxyoctanoic acid, 3-hydroxy-3-methyl-octanoic acid, 2- nonenoic acid, 2-methyl-2-nonenoic acid, 3-methyl-2-nonenoic acid, nonanoic acid, 2-methylnonanoic acid, 3- methylnonanoic acid, 3-hydroxynonanoic acid, 3-hydroxy-3-methylnonanoic acid, 2-decenoic acid, 2-methyl-2-decenoic acid, 3-methyl-2-decenoic acid, decanoic acid, 2-methyldecanoic acid, 3- methyldecanoic acid, 3-hydroxydecanoic acid, 3-hydroxy-3-methyldecanoic acid, 10-hydroxydecanoic acid, 2-undecenoic acid, 2-methyl-2-undecenoic acid, 3-methyl-2-undecenoic acid, undecanoic acid, 2- methylundecanoic acid, 3-methylundecanoic acid, 3-hydroxyundecanoic acid, 3-hydroxy-3-methylundecano oh acid, dodecanoic acid, 2-gidroksidodekanovoy acid, tridecanoic acid, 2-gidroksidodekanovoy acid and tridecanoic acid,

g) conjugated products of 3-methyl-3-sulfanylhexan-1-ol and, in particular, the compounds of the following formula (4):

R ₄ -X ₂ -C (X ₁ ) -ALK-X ' ₂ -C (X' ₁ ) -CH (X '' ₂ H) -ALK'-S-R ' ₄ (4)

wherein:

R ₄ and R ' ₄ , which may be the same or different, represent a hydrogen atom, a linear or branched (C ₁ -C ₈ ) alkyl, or a linear or branched (C ₂ -C ₈ ) alkenyl group, such as methyl, which is optionally substituted with a hydroxyl group, preferably R ₄ represents a hydrogen atom, and R ' ₄ represents a (C ₁ -C ₄ ) alkyl group optionally substituted with a hydroxyl group,

ALK and ALK ', which may be the same or different, are a hydrogen atom, a linear or branched (C ₁ -C ₈ ) alkyl, or a linear or branched (C ₁ -C ₈ ) alkylene group, optionally substituted with a -X ₂ -R group ₄ , c R ₄ ,

X ₁ and X ₂ , which may be the same or different, such as previously defined, preferably X ₁ = X ₂ = O,

X ' ₁ and X' ₂ and X '' ₂ , which may be the same or different, such as defined for X ₁ and X ₂ , respectively, preferably, X ' ₁ = X' ₂ = NH and / or X ' ₁ = O.

In particular, aromatic compounds of this class are selected from the following compounds:

S- (1-hydroxy-3-methylhexan-3-yl) cysteine glycine, S- (1-hydroxy-2-methylhexan-3-yl) cysteine glycine, S- (1-hydroxy-2-methylbutan-3-yl) cysteine glycine S- (1-hydroxypentan-3-yl) cysteine glycine, S- (1-hydroxybutan-3-yl) cysteine glycine, S- (1-hydroxy-3-methylpentan-3-yl) cysteine glycine, S- (1-hydroxy -3-methylbutan-3-yl) cysteine glycine, S- (1-hydroxyhexan-3-yl) cysteine glycine and S- (1-hydroxy-2-methylhexan-3-yl) cysteine glycine,

h) ketone compounds such as 6,10-dimethyl-5,9-undecadien-2-one or tridecanone,

i) alkanols such as isopentanol or 1-decanol.

More specifically, fragrant molecules capable of being effectively captured by the cyclodextrin polycondensates of the present invention are selected from 3-methyl-2-dexenoic acid, octanoic acid, nonanoic acid, decanoic acid, 6,10-dimethyl-5,9-undecadien-2-one, tridecanone, isopentanol and 1-decanol.

Among the compounds that can cause discomfort with keratin substances, we can mention the sweat (exocrine or apocrine) produced by sweat glands during sweating. Sweat contains mainly water. It also contains minerals, in addition to lactate, which is an ionized form of lactic acid, and urea.

The strong dehumidification ability of the cyclodextrin polycondensates of the present invention makes it possible to effectively capture sweat components when these polycondensates are applied to keratin substances.

Thus, an object of the present invention is a method for cosmetic treatment of odors of human sweat and / or body, which consists in applying to the surface of a human keratin substance a composition comprising, in a physiologically acceptable medium, at least one cyclodextrin polycondensate as previously defined.

Among the substances that can cause discomfort with keratin substances, mention may be made of excess sebum produced by the sebaceous glands of oily skin or individuals having oily hair. Human lard usually contains fats containing squalene (approximately 15%), ester waxes (approximately 25%), cholesterol esters (approximately 2%), triglycerides (approximately 57%) and cholesterol (approximately 1%).

The strong dehumidification ability of the cyclodextrin polycondensates of the present invention makes it possible to effectively capture excess sebum when applying said polycondensates to the surface of the skin, hair or scalp, and to treat oily skin and oily hair against dandruff, and the appearance of oily dandruff, and to prevent arising from this skin and hair disorders.

Thus, the next subject of the present invention is a non-therapeutic cosmetic method for the care and / or purification of a keratinous substance of a person who is fatty or with a tendency to oily, including at least. one stage of topical application to said keratin substance, a composition comprising, in a physiologically acceptable medium, at least one cyclodextrin polycondensate as previously defined.

Useful Agents

The cyclodextrin polycondensates of this invention can also be used to trap at least one beneficial agent as previously described. These beneficial agents can be selected from:

a) fatty substances

Fatty substances are widely used in the preparation of pharmaceutical, cosmetic and / or food compositions. They can be selected from the group including:

i) natural oils of vegetable, animal and marine origin, such as olive oil, sesame oil, argan oil, palm oil, soybean oil, waida oil, babassu oil, aloe vera, avocado oil, allantoin, bisabol, grape seed oil, apricot oil , wheat germ oil, almond oil, peanut oil, macadamia nut oil, sea buckthorn oil, evening primrose oil, borage oil, ginger oil, geraniol, unabi oil, mink fat or lanolin,

ii) synthetic oils,

iii) mineral oils such as isohexadecane, para-isoparaffin, ceresin or petrolatum,

iv) hydrogenated oils,

v) silicone oils,

vi) hydrocarbon compounds such as paraffin oil,

vii) terpenes

viii) squalene.

ix) saturated or unsaturated fatty acids, such as myristic acid,

x) fatty acid esters,

xi) waxes, beeswax, jojoba oil, which is actually liquid wax, ester waxes,

xii) fatty alcohols, such as myristyl alcohol, cetyl alcohol, stearyl alcohol or myricyl alcohol,

xiii) oils, such as shea butter or cocoa butter,

xiv) or a mixture thereof.

One of the possible uses according to this invention is the transfer of fatty substances for cosmetic use or for use in food or dietetic cosmetic use, such as nutritional supplements.

b) Flavors and flavor enhancers

One of the possible uses according to this invention is the transfer of flavoring substances and / or flavor enhancers for use in food or for dietetic cosmetic use, such as nutritional supplements.

1) Flavors

Among the flavors, the following flavors selected from:

i) from substances specified in the official list established by the European Council in the publication Substances arômatisantes et sources naturelles de matières arômatisantes [Flavors and natural sources of flavoring substances], vol. 1, 4 ^th edition, 1992, Maisonneuve,

ii) Of the substances listed on the FEMA / GRAS Official Lists published by the United States Food and Drug Administration (FDA).

Flavor enhancers

The European Union defines flavor enhancers in the list of nutritional supplements by number E. They are numbered from E620 (glutamic acid) to E641 (L-leucine).

Among the flavor enhancers, mention may be made of

i) glutamates such as glutamic acid (E620), monosodium glutamate (E621), monopotassium glutamate (E622), calcium diglutamate (E623), ammonium glutamate (H624) or magnesium diglutam (E625),

ii) guanilates, such as guanilic acid or guanisine monophosphate (E626), disodium guanilate (E627), dipotassium guanilate (E628) or calcium guanilate (E629),

iii) inosinates, such as inosinic acid (E630), disodium inosinate (E631), dipotassium inosinate (E632) or calcium inosinate (E633).

Mention may also be made of calcium 5′-ribonucleotide (E634), disodium 5′-ribonucleotide (E635), maltol (E636), ethyl maltol (E637), glycine (E640) and L-leucine (E641).

Mention may also be made of the following additives considered to be enhancers: lactic acid (acidifier) (E270), sweeteners such as Acesulfame-K (E950), aspartame (E951), thaumatin (E957), neohesperidine dihydrochalcon (E959), neotam (E961) or erythritol (E968).

c) Flavors

It is understood that the term "flavoring substance" means any fragrant substance or incense capable of spreading a pleasant aroma.

Fragrances are compositions, in particular, containing the starting materials described by S. Arctander, Perfume and Flavor Chemicals (Montclair, NJ, 1969), in S. Arctander, Perfume and Flavor Materials of Natural Origin (Elizabeth, NJ, 1960) and in Flavor and Fragrance Materials - 1991, Allured Publishing Co., Wheaton, III.

In addition, they can be natural products, for example, essential oils, absolutes, resinoids, resins, concrete and / or synthetic products (terpene or sesquiterpene hydrocarbons, alcohols, phenols, aldehydes, ketones, ethers, acids, esters, nitriles or peroxides, which may be saturated or unsaturated, and aliphatic or cyclic).

According to the definition given in the international standard ISO 9235, and adopted by the European Pharmacopoeia Committee, essential oil is an aromatic product, usually having a complex composition, obtained from botanically defined plant materials, either by steam distillation, or by dry distillation, or by appropriate mechanical means without heating (cold pressing). Essential oil is usually separated from the aqueous phase by a physical method, which does not lead to any significant change in composition.

Among the essential oils that can be used according to this invention, mention may be made of oils obtained from plants belonging to the following botanical families:

Spruce or pine: coniferous trees; Amaryllis; cashew; Annon: Ylang-Ylang; celery (for example, umbrella): dill, angelica, coriander, marine critmum, carrots, parsley; aronnikovye; kirkazonovye; asters: yarrow, wormwood, chamomile, immortelle; birch; cabbage; burser: boswellia; cloves; canelic; Caesalpinium: kopaya (Kapay balm); haze; cistus: rock rose; sedge; dipterocarp; heather: gaulteria (grushanka); euphorbiaceae; legumes; geraniums: geranium; clusian; witch hazel; Hernandian; St. John's wort: St. John's wort; iris nutty; clear: thyme, oregano, monarda, savory, basilica, marjoram, mint, patchouli, lavender, sage, catnip, rosemary, hyssop, lemon balm; laurel: ravensara, magnolia, dalbergia, cinnamon, verbena; lily: garlic; magnolia: magnolia; Malvaceae; melium; monimium; mulberries: hemp, hops; worldly; nutmeg: nutmeg; myrtle: eucalyptus, tea tree, paper maple, cayeput, bacchus, cloves, myrtle; olives; pepper: pepper; pittospore; Cereals: lemon mint, lemon cereal, vetiver; buckwheat; buttercups; pink roses; madder; routine: all citrus plants; willow; Santal: sandalwood; stone-breaking; lemongrass; styrax: benzoin; wolfs: eagle tree; linden; valerian: valerian, aralia; verbena: lanthanum, verbena; violet; ginger: galangal, turmeric, cardamom, ginger; leafy leaves.

You can also mention essential oils extracted from flowers (lily, lavender, rose, jasmine, ylang-ylang, neroli), from stems and leaves (patchouli, geranium, petigren), from fruits (coriander, anise, cumin, juniper), from peel (bergamot, demon, orange), from the roots (angelica, celery, cardamom, iris, rattan, ginger), from wood (pine, sandalwood, guaiac wood, cedar rose, camphor), from herbs and cereals ( tarragon wormwood, rosemary, basil, lemon grass, sage, thyme), from needles and branches (spruce, fir, pine, cedar) of resins and (galbanum, elemi, benzoin, myrrh, frankincense, opopanaks).

Examples of aromatic substances are, inter alia, geraniol, geranyl, farnesol, bonreol, bornylacetate, linolool, linalyl acetate, linalilpropionat, linalilbutirat, tetragidrolinolool, citronellol, tsitronellilatsetat, tsitronellilformiat, tsitronellilpropionat, digidromirtsenol, digidromirtsenilatsetat, tetragidromirtsenol, terpineol, terpinyl acetate, nopol, nopilatsetat, nerol, non-ethyl acetate, 2-phenylethanol, 2-phenylethyl acetate, benzyl alcohol, benzyl acetate, benzyl salicylate, styranyl acetate, benzyl benzoate, amyl salicylate, dimethyl benzyl carbin l, trichloromethylphenylcarbinyl acetate, p-tert-butylcyclohexyl acetate, isononyl acetate, vetiveryl acetate, vetiverol, α-hexylcinnamaldehyde, 2-methyl-3- (p-tert-butylphenyl) propanal, 2-methyl-3- (p-isopropylphenyl) propane, ) propanal, 3- (p-tert-butylphenyl) propanal, 2,4-dimethylcyclohex-3-enylcarboxaldehyde, tricyclodecenyl acetate, tricyclodecenylpropionate, 4- (4-hydroxy-4-methylpentyl) -3-cyclohexenecarboxaldehyde, 4- (4-methyl-3 -pentenyl) -3-cyclohexenecarboxaldehyde, 4-acetoxy-3-pentyltetrahydropyran, 3-carboxymethyl-2-pentylcyclopentane, 2-p-4-heptylcyclopentanone, 3-methyl-2-pentyl-2-cyclopentenone, menton, carvone, tagetone, geranylacetone, n-decanal, n-doo-channel, 9-decen-1-ol, phenoxyethyl isobutyrate, phenylacetaldehyde dimethyl acetal, diethyl phenylacetaldehyde, geranonitrile, citronellonitrile, cedryl acetate, 3-isocamphylcyclohexanol, cedryl methyl ether, isolongifolanone, acbepinonitrile, aubepin, heliotrope, coumarin, eugenol, vanillin, diphenyl ionone, citronone ionone, citronone ionone hydrochloride, citronone ionone hydrochloride, citronone ion hydrochloride 3-hexenol and its esters, musk indans, musk tetralins, musk isochromanes, macrocyclic ketones, musk macrolactones, aliphatic musks, ethylene brassilate and pink essence and mixtures thereof.

Another possible application is, for example, the transfer of fragrances for the production of perfumes (perfumes, eau de toilette, eau de parfum, aftershave), cosmetic products for the care and / or purification of keratin substances, in particular human keratin substances, makeup products, for the production of clothes, shoes, outsoles and products for their care, in products intended for animal hygiene, in products intended for the care of children (napkins, diapers), in products intended for personal hygiene (tampons, pads, towels), in products for hygienic use, and in food and agricultural products.

d) Pharmaceutically active ingredients

The term “pharmaceutically active ingredient” is intended to mean a molecule having a therapeutic and / or prophylactic effect.

For example, it can be any molecule with therapeutic properties that is part of a drug composition. Mention may be made, for example, of non-steroidal anti-inflammatory drugs (NSAIDs), abortion drugs, alpha blockers, alpha2 agonists, aminosides, analgesics, anesthetics, topical analgesics, anorexigenic drugs, 5HT3 antagonists, calcium antagonists, antianginal drugs antibiotics, anticholinergics, anticholinesterase drugs, antidiabetic drugs, anti-diarrhea drugs, antidepressants, antihistamines, antihypertensive drugs, anti fungal preparations, antimalarial drugs, antiparasitic drugs, antipsychotic drugs, antipyretic drugs, antiretroviral drugs, antiseptic drugs, antispasmodics, antiviral drugs, antiemetic drugs, antiepileptic drugs, anxiolytic drugs, barbiturates, benzodiazepines, bronchodilators, corticosteroids, b , diuretics, loop diuretics, osmotic diuretics, sedatives, glucocorticoids, psycho active drugs, hypnotics, immunosuppressants, carbonic anhydrase inhibitors, neuraminidase inhibitors, proton pump inhibitors, TNF inhibitors, serotonin selective reuptake inhibitors, HMG-CoA reductase inhibitors (or statins), keratolytics, laxatives, mineralocorticoids, neuroleptics, muscle drugs, antispasmodics, stimulants, sedatives, tocolytic drugs or vasodilators. This list is not exhaustive and applies to any therapeutically active ingredients known to specialists in this field.

e) Cosmetically active ingredients

The term “cosmetically active ingredient” is intended to mean any molecule that has a hygienic, caring, make-up or coloring effect, leading to improved well-being and / or giving a more attractive appearance to the keratinous substance of the person to whom the composition is applied.

Therefore, cosmetically active agents can be selected from any substances that fall under this definition and which are present in products such as

i) hygiene products: makeup removers, toothpastes, deodorants, antiperspirants, shaving gels, bath products (bath foam, bath oil, bath salts), intimate cleansing gels, soaps, shampoos,

ii) care products: anti-wrinkle cream, day cream, night cream, moisturizer, eau de toilette, exfoliating agent, milk, cosmetic mask, lip balm, tonic,

iii) hair care and / or treatment products, such as hair styling products, curling products, conditioning agents: conditioner, hair straightener, gel, oil, varnish, mask,

iv) makeup products: foundation, eyeliner pencil, face powder, foundation, eyebrow pencil, mascara, powder, skin whitening agent, lipstick, nail polish,

v) perfume: cologne, eau de toilette, perfume,

vi) tanning products: artificial tanning products, creams, lotions, oils or solutions after tanning and for tanning,

vii) Shaving and hair removal products: after-shave cream, hair remover, foam and shaving gels.

In the range of active ingredients for the care of keratinous substances of a person, such as skin, lips, scalp, hair, eyelashes or nails, examples that can be cited include:

- vitamins and derivatives or their precursors, individually or in the form of mixtures,

- antioxidants,

- cleaning products

- Hair Dye,

- conditioning agents

- means for straightening and / or straightening and / or hair styling,

- traps of free radicals,

- means for controlling pollutants,

- photoprotective agents, such as organic protective agents, inorganic UV protective agents,

- means for artificial tanning,

- anti-glycation agents

- sedatives

- hair removal products,

- deodorants,

- antiperspirants,

- essential oils,

- inhibitors of NO synthase,

- funds that stimulate the synthesis of dermal and epidermal molecules, and / or prevent their destruction,

- agents that stimulate the proliferation of fibroblasts,

- anti-wrinkle products,

- refreshing products

- means for tensioning,

- matting agents,

- depigmenting agents,

- means for pigmentation,

- keratolytic agents

- desquamating agents,

- moisturizers

- antimicrobial agents,

- means for weight loss,

- funds acting on energy metabolism in cells,

- insect repellents,

- antagonists of substance-P or CGRP,

- means for combating hair loss,

- anti-wrinkle products,

- anti-aging products.

Cyclodextrin polycondensates according to this invention can be very effectively used in cosmetic or dermatological compositions containing, in addition, a physiologically acceptable medium.

The amount of cyclodextrin polycondensate present in these compositions undoubtedly depends on the type of composition and on the desired properties, and can vary over a very wide range, usually from 0.1% to 100 mass%, preferably from 0.5% to 95 mass% in particular, from 1% to 70 mass%, or even from 1.5% to 50 mass%, and even better, from 2% to 20 mass%, based on the total weight of the composition.

Thus, the composition may contain, depending on the intended use, components standard for this type of composition.

The composition according to the invention may preferably contain at least one fatty phase, which may include at least one compound selected from volatile or non-volatile carbon, hydrocarbon, fluorine and / or silicon oils, waxes and / or mineral solvents , animal, vegetable or synthetic origin, individually or in the form of a mixture, provided that they form a stable homogeneous mixture and are compatible with the intended use.

For the purposes of the invention, it is understood that the term “volatile” means any compound that is capable of vaporizing upon contact with keratin substances for less than one hour at ambient temperature (25 ° C) and atmospheric pressure (1 atm). In particular, this volatile compound has a non-zero vapor pressure at ambient temperature and atmospheric pressure, varying from 0.13 Pa to 40,000 Pa (from 10 ^-3 to 300 mmHg), in particular, varying from 1.3 Pa to 13000 Pa (from 0.01 to 100 mm Hg), and more specifically, varying from 1.3 Pa to 1300 Pa (from 0.01 to 10 mm Hg).

On the contrary, it is understood that the term "non-volatile" means a compound remaining on human keratin substances at ambient temperature and atmospheric pressure for at least one hour, and which, in particular, has a vapor pressure of less than 10 ^-3 mm RT St (0.13 Pa).

The fatty phase may comprise from 1% to 99 mass% of the composition, in particular from 5% to 95 mass%, in particular from 10% to 90 mass%, or even from 20% to 85 mass% of the total weight of the composition.

The composition may also include other ingredients commonly used in cosmetic compositions. Such ingredients can be selected from antioxidants, flavorings, essential oils, preservatives, cosmetically active components, moisturizers, vitamins, ceramides, sunscreens, surfactants, spreading agents, moisturizing components, dispersants, foaming inhibitors, neutralizing agents, stabilizers, polymers and, in particular, liposoluble film-forming polymers, and mixtures thereof.

Of course, specialists in this field will take care of the choice of this or these optional additional compounds (compounds) and / or their quantities so that the intended addition does not have, or practically does not adversely affect, the advantageous properties of the composition for use according to this invention.

The compositions of this invention may have any suitable form of a cosmetic or dermatological composition.

Specialists in this field can choose the appropriate galenic form, as well as the method of its preparation, based on their general knowledge, taking into account both the nature of the components used, in particular, their solubility in the base, and the intended use of this composition.

The invention is illustrated in more detail by the following examples.

Production Examples

Information regarding the various starting materials used in the following examples is summarized in the following table.

INCI name Provider Tradename β-cyclodextrin Wacker CAVAMAX W7 FOOD α-cyclodextrin Wacker CAVAMAX W6 FOOD GRADE® γ-cyclodextrin Wacker CAVAMAX W8 FOOD GRADE® Hydroxypropyl cellulose 80K KLUCEL® Maleic Anhydride ALDRICH M625® Lemon acid DSM Citric Acid Monohydrate Sodium dihydrogen phosphate Merck Sodium Dihydrogen Phosphate Dehydrate (RECTAPUR®) Glycerol ALDRICH Glycerol

Synthesis of cyclodextrin polycondensates

Example 1a

β-Cyclodextrin polycondensate 1a was obtained after extrusion of β-cyclodextrin (CD) in the presence of hydroxypropyl cellulose (HPC), citric acid and sodium dihydrogen phosphate (DHFN). The proportion of each component is indicated below in mass percent:

Polymer β-CD GOC Lemon acid Sodium dihydrogen phosphate 1a 45.16 thirty 22.58 2.28

According to this preparation method, all the ingredients that make up part of the composition for producing polycondensate 1a are introduced at the same time into an extrusion apparatus (twin-screw extruder Clextral BC 21) at a temperature of 170 ° C.

The extrusion conditions are summarized below:

Temperature (° C) Exhaust ratio
(rpm) Extrusion Flow Rate (kg / h) 170 115 3

After grinding, hemicondexate 1a was obtained in the form of a cream-colored powder with an average particle size of 10 μm.

Protocol for measuring swelling in water:

2 g of ground polycondensate 1a were suspended in 20 g of demineralized water with gentle stirring for 24 hours at ambient temperature. The suspension was centrifuged to separate the supernatant and the solids content of the centrifuge was determined by thermal equilibrium. % The degree of swelling was obtained by calculating the ratio of the evaporated mass / dry weight x 100.

The acid number of cyclodextrin polycondensate 1a is 150 mg of potassium hydroxide per g of polycondensate, and the degree of swelling in water is 805%.

Examples 1b, 2a, 2b and 2c

The following cyclodextrin polycondensates (compositions and synthesis conditions) were synthesized as follows: the yields of each component are indicated below in the form of mass percent:

Cyclodextrin Poly Condensates β-CD α-CD γ-CD GOC Lemon acid Maleic Anhydride DHFN 1b 44.71 0 0 29.7 22.35 one 2.24 2a 40.63 0 4,51 thirty 22.58 0 2.28 2b 31.61 13.53 0 thirty 22.58 0 2.28 2c 31.61 9.02 4,51 thirty 22.58 0 2.28-

The extrusion conditions, the acid number of the obtained cyclodextrin polycondensates, as well as the degree of swelling in water, determined under the same conditions as in example 1a, are summarized below.

Cyclodextrin Poly Condensates Temperature (° C) Extraction rate (r / min) Extrusion Flow Rate (kg / h) Acid number The degree of swelling in water 1b 170 110 3 161 740% 2a 180 110 3 127 520% 2b 175 130 3 130 440% 2c 180 110 3 128 530%

Comparative example A synthesis of cyclodextrin polycondensate by the method of patent EP1165621B1

In a 2 liter round bottom flask was placed 1 liter of demineralized water, 50 g of sodium dihydrogen phosphate NaH ₂ PO ₄ , 500 g of citric acid monohydrate and 1 kg of β-cyclodextrin. The reaction medium was stirred and heated to 60-70 ° C to completely dissolve the starting compounds. The resulting solution was transferred to a crystallizer, the size of which was chosen so that the height of the liquid was approximately 6 cm. The crystallizer was placed in an oven heated to 100 ° C for 80 h (a soft gel was obtained). After that, the temperature was raised to 140 ° C for 4 hours, and then returned to ambient temperature. The resulting solid was separated from the mold and then finely ground using a knife mill such as a coffee grinder. Its analysis was performed by 2D DOSY NMR, which allowed the detection of covalent grafting of citric acid onto β-cyclodextrin to form an oligomer with a diffusion coefficient of 173 μm ² / s, which corresponds to an estimated molecular weight of approximately 3800 g / mol. Its acid number is 195 mg of potassium hydroxide per g of polycondensate, and its degree of swelling in water is 0%, since it is completely soluble at ambient temperature (solubility greater than 30%).

Trapping bad smelling substances

The analysis was carried out by two-dimensional gas chromatography (GC × GC / MS) in order to evaluate and display the ability of cyclodextrin half-condensates according to this invention to capture / trap bad smelling substances arising from the production of sweat.

Test report

50 μl of sweat was placed in a 6 ml Headspace® flask and 2, 5, 10, or 25 mg of cyclodextrin condensate for evaluation was added. The flask was closed (Al / Si septum) and placed in an oven at 37 ° C for 24 hours, and then acidified by adding 50 μl of 1N HCl.

A control sample of sweat was used: the same protocol, but without the addition of cyclodextrin polycondensate.

Solid-phase microextraction (SPME) was performed using PDMS / DVB 65 μm fiber for 45 minutes at 37 ° C. The fiber was stripped in an input device of a GC2 chromatograph.

Evaluation of the display of molecules of bad smelling substances released with sweat was performed by mass spectrography, respectively, for a control sample of sweat and for sweat incubated in the presence of cyclodextrin polycondensate 1a.

Using the GC-HX / MS

Gas Chromatograph 1

Auto Dispenser: GC-2010 and AOC-20i (Shimadzu)

Column: Rxi-5ms (Restek): 30 m × 0.25 mm ID × 0.1 μm off

Program temperature: 60 ° C (1 min) → 270 ° C at 6 ° C / min

Constant linear velocity: 27 cm / s (initial helium pressure: 36.1 psi (249 kPa))

Input mode: with a separator (ratio of a separator: 10/1)

Temperature: 250 ° C

Input Mode: Solid Phase Microextraction

Transition line temperature: 280 ° С

Gas Chromatograph 2

Auto Dispenser: GC-2010 and AOC-20i (Shimadzu)

Column: Rtx-200 (Restek): 1.5 m × 0.1 mm ID × 0.1 μm off

Program temperature: 40 ° C (2 min) → 245 ° C at 6 ° C / min

Mass spectrometer:

MS detector QP2010 plus (Shimadzu)

Converter (Chrom Square)

Winding machine correction: 0.5 s

Scale 20000 → 1.0E6

The results obtained for polycondensate 1A

It was noticed that with the addition of 25 mg of polycondensate, the following bad-smelling compounds formed later were completely captured: 3-methyl-2-hexenoic acid, octanoic acid, 6,10-dimethyl-5,9-undecadien-2-one, tridecanone, nonanoic acid, decanoic acid, isopentanol and 1-decanol

Encapsulation of fragrances

The encapsulating properties of the β-cyclodextrin polymer were determined and compared with a single β-cyclodextrin, but also

- with β-cyclodextrin polycondensate of comparative example A described above, and

- with β-cyclodextrin polycondensate crosslinked with epichlorohydrin containing 54% CD sold by Cyclolab under the name CY-2009® (comparative example B).

Encapsulating Ability Measurement Protocol

To 1 g of each of the test compounds was added 5 g of dihydromyrceneol (an aromatic substance), and then the mixture was stirred under low light for 24 hours. After centrifugation to remove non-impregnated aromatic substance and drying in air at ambient temperature in a dry atmosphere for 214 hours, the impregnated compound was heated at 150 ° C using thermal equilibrium, also known as a halogen desiccator (Mettier Toledo model HG63) to constant weight.

Thus, the amount of dihydromyrcene encapsulated in the matrix of each of the tested compounds was determined.

An amount of 0.5 g and 1 g of the impregnated compound was precipitated onto a cup, and then heating was started, with weight loss recorded every 2 minutes. When a constant mass was reached, the apparatus automatically stopped heating, and the following data were obtained: initial mass, final mass,% solids content at 2-minute intervals, total duration of evaporation.

The results of encapsulation of dihydromyrcene according to the previously described protocol were summarized in the following table:

Material investigated The amount of encapsulated
fragrance (%) β-Cyclodextrin polycondensate 1a (invention) 68 β-cyclodextrin eighteen Comparative β-cyclodextrin polycondensate A eighteen Comparative β-cyclodextrin polycondensate B eighteen

It was noted that the β-cyclodextrin polycondensate of Example 1a according to the present invention exhibits a degree of encapsulation of an aromatic substance that is 3.7 times greater than the degree of encapsulation of β-cyclodextrin, the degree of encapsulation of comparative β-cyclodextrin polycondensate A, and the degree of encapsulation of comparative β-cyclodextrin polycene condensate .

Example 1: Composition of deodorant and antiperspirant

Ingredients Quantity in mass% Cyclodextrin Polycondensate 1a 5% Dimethicone (s) dimethicone cross-polymer (Dow Corning (R) 9041 mixture of silicone elastomers) 2% Hydrogenated Polydecene (SILKFLO 366 POLYDECENE-INEOS) 26.3% PPG-14 butyl ether 2% Tribegenin (SYNCROWAX HRC-PA-CRODA) 6% C ₁₈ / C ₃₆ fatty acid triglycerides (SYNCROWAX HGLC-PA (MH) -CRODA) 1.5% Dimethicone 10 cSt Qs 100

This composition exhibits good antiperspirant effectiveness and good deodorant effectiveness.

Comparative tests of cyclodextrin polycondensate according to the invention and cyclodextrin polycondensates according to application WO01 / 48025

Examples 1c, 3a, 3b

The following cyclodextrin polycondensates (composition and synthesis conditions) were synthesized in the following way: the proportion of each component is indicated as mass percent below:

Cyclodextrin Polycondensate β-CD GOC Lemon acid BELCLENE 283® DHFN 1c (invention) 45.1 29.8 22.8 - 2,3 3a (comparative) 65.9 29.8 - 2 2,3 3b (comparative) 45.1 29.8 - 22.8 2,3

The extrusion conditions are presented below.

Cyclodextrin Polycondensate Temperature (° C) Extraction rate (r / min) Extrusion Flow Rate (kg / h) 1c 170 90 3,1 3a 170 90 2

3b unsuitable for use

Fragrance Encapsulation

The encapsulating properties of the β-cyclodextrin polymer 1c were determined and compared with the β-cyclodextrin polycondensate 3a described above, and

Encapsulation Capability Measurement Protocol

To 1 g of each of the test compounds was added 5 g of dihydromyrceneol (an aromatic substance), and then the mixture was stirred in low light for 24 hours. After centrifugation to remove non-impregnated aromatic substance, drying in air in a dry atmosphere at ambient temperature for 24 hours, the impregnated compound was heated at 150 ° C using thermal balance, also known as a halogen desiccator (Mettler Toledo HG63 model) to constant weight.

Thus, the amount of dihydromyrcene encapsulated in the matrix of each test compound was determined.

An amount of 0.5 g to 1 g of the impregnated compound was precipitated on a cup, and then heating was started, recording the weight loss every 2 minutes. When a constant mass was reached, the apparatus automatically stopped heating and produced the following data: initial mass, final mass,% solids content at 2-minute intervals, total duration of evaporation.

The results of the encapsulation of dihydromyrcene according to the protocol described above are presented in the following table:

Substance tested The amount of encapsulated fragrance (%) β-Cyclodextrin polycondensate 1c (invention) 68

Comparative β-cyclodextrin polycondensate 3a twenty

It was noted that the β-cyclodextrin polycondensate of Example 1c according to the present invention exhibits a degree of encapsulation of an aromatic substance that is 3.4 times higher than the degree of encapsulation of comparative β-cyclodextrin polycondensate 3a.

Odor reduction

Test protocol

The amount of sweat was extracted from a group of 6 male volunteers with a more or less pronounced unpleasant odor.

1 ml of sweat was placed in a 10 ml Headspace® flask, and 10 or 50 mg of the cyclo-texter condensate was added for evaluation at a concentration of 10 mg / ml (1 mass%) or 50 mg / ml (5 mass%), respectively.

Samples were placed in an oven at 35 ° C in a stirrer, stirring at a speed of 140 rpm, and incubated for 24 hours.

After incubation, samples were evaluated and compared with two control sweat samples at the same time: a positive sweat control containing 0.1 mass: aluminum hydrochloride and a negative sweat control containing only sweat.

Assessment of the images was carried out by 2 independent experts.

The effectiveness of the deodorant was evaluated by the method of “test by smell” according to the following criteria:

- sweat odor intensity (school from 0: low intensity odor to 10: unpleasant odor of extremely strong effectiveness),

- residual odor (scale from 0: slight unpleasant odor to 10: very strong residual unpleasant odor),

- hedonistic rating (scale from 0: extremely unpleasant odor to 10: very strong residual unpleasant odor).

Test sample Odor intensity Residual odor Hedonistic assessment One control sweat 8.7 9.7 0,0 Control sweat sample with 0.1% aluminum hydrochloride 3.0 2.0 5,0 1% cyclodextrin polycondensate 1c (invention) 4.3 5,0 3.3 5% cyclodextrin polycondensate 1c (invention) 4.0 3.0 4.0 1% comparative cyclohextrin polycondensate 3a 7.4 8.0 1,0 5% comparative cyclohextrin polycondensate 3a 6.7 6.7 1,0

It was noted that the cyclodextrin polycondensate 1c according to the present invention has good deodorizing effectiveness, which can reach the level of aluminum salt, in comparison with the comparative cyclodextrin polycondensate 3a having low efficiency.

Claims (66)

1. Water-insoluble cyclodextrin polycondensate, which is obtained by mixing: (A) at least one cyclodextrin; and (B) at least one saturated or unsaturated, or aromatic, linear or branched or cyclic polycarboxylic acid and / or at least one ester or one acid anhydride or one halide of said polycarboxylic acid, and (C) at least one thermoplastic polyol as one polymer and (D) optionally, in the presence of at least one esterification catalyst and / or (E) optionally at least one cyclic polycarboxylic acid anhydride selected to be different from the polycarboxylic acid anhydride of paragraph (B), and / or (F) optionally at least one non-polymeric polyol containing from 3 to 6 hydroxyl groups in the apparatus, functioning with a shear force sufficient to bring the specified mixture into a thermoplastic state, at a temperature of from 100 to 250 ° C. 2. The polycondensate according to claim 1, in which the ratio of the number of moles of polycarboxylic acid to the number of moles of cyclodextrin is from 0.5 to 5. 3. The polycondensate according to claim 1 or 2, having an acid number expressed in mg of potassium hydroxide per g of polycondensate, which is greater than or equal to 20. 4. The polycondensate according to claim 1, characterized in that it exhibits a degree of swelling in water, measured at 20 ° C, which is greater than or equal to 100%, in particular, from 100% to 1000%. 5. The polycondensate according to claim 1, wherein the cyclodextrin is selected from α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin and mixtures thereof, and even better is β-cyclodextrin. 6. The polycondensate according to claim 1, in which the polycarboxylic acid is aliphatic, saturated and linear and contains from 2 to 36 carbon atoms, in particular from 3 to 18 carbon atoms or even from 4 to 12 carbon atoms, or, alternatively, polycarboxylic the acid is aromatic and contains from 8 to 12 carbon atoms, more preferably it contains from 2 to 4 COOH groups, and more preferably it is selected from citric acid, aconitinic acid, tartaric acid, 1,2,3-propanetricarboxylic acid and 1,2 , 3,4-butanetetracarboxylic acid, in individually or in mixtures, preferably individually, and even more preferably citric acid. 7. The polycondensate according to claim 1, in which i) the ester of said polycarboxylic acid is a C ₁ -C ₄ alkyl ester of a mono-, di-, tri- or tetraester, and in particular methyl, ethyl, isopropyl or n-butyl esters, and more preferably aliphatic methyl or ethyl esters, saturated, linear polyacids containing from 2 to 4 COOH groups and containing from 2 to 36 carbon atoms, in particular from 3 to 18 carbon atoms, or even from 4 to 12 carbon atoms, or, alternatively, an aromatic acid containing from 8 to 12 carbon atoms, ii) the acid anhydride is selected from a) mixed anhydrides with C ₂ -C ₄ carboxylic acid, in particular acetic acid, propionic acid or butyric acid, preferably acetic acid, or b) cyclic anhydrides such as phthalic anhydride, trimellitic anhydride, maleic anhydride, succinic anhydride or anhydride of N, N, N ', N'-ethylenediamine tertoacetic acid. iii) the acid halide is selected from the acid halides and bromides of the specified polycarboxylic acid, preferably the halides of aconitinic acid, tartaric acid, 1,2,3-propanetricarboxylic acid and 1,2,3,4-butanetetracarboxylic acid, and most preferably the acid chlorides of these acids. 8. The polycondensate of claim 1, wherein the thermoplastic polyol is selected from polyether polyols, ester polyols, polycarbonate polyols, polyamide polyols, polyurethane polyols, polyalkylene polyols, polycaprolactone polyols and polysaccharides, and preferably polysaccharides, and more preferably cellulose derivatives, and even more preferably hydroxypropyl cellulose and hydroxyethyl cellulose, and most preferably one hydroxypropyl cellulose. 9. The polycondensate according to claim 1, in which cyclic polycarboxylic acid anhydride, if present, corresponds to one of the following formulas:

in which groups A and B are, independently of each other: - a hydrogen atom, a saturated or unsaturated, linear, branched and / or cyclic, or, alternatively, aromatic carbon-based radical containing from 1 to 16 carbon atoms, in particular from 2 to 10 carbon atoms, or even from 4 to 6 carbon atoms, in particular methyl or ethyl, - or, alternatively, A and B together form a saturated or unsaturated, or even an aromatic ring containing a total of 5 to 7, and in particular 6 carbon atoms, more preferably A and B represent a hydrogen atom or together form an aromatic cycle containing in total 6 carbon atoms, more preferably individually or as a mixture, phthalic anhydride, trimellitic anhydride, maleic anhydride and succinic anhydride, and even more preferably one maleic anhydride. 10. The polycondensate according to claim 1, wherein the esterification catalyst, if present, is selected from dihydrogen phosphates, hydrogen phosphates, phosphates, hypophosphites and alkali metal phosphites, alkali metal salts with polyphosphoric acids, carbonates, hydrocarbons, acetates, borates and alkali metal or alkaline earth hydroxides metals, aliphatic amines and aqueous ammonia, optionally in combination with an inorganic solid carrier such as alumina, silica gels, aluminosilicates, zeolites, titanium oxides or oxides of zirconium, sulfones acid or titanates, and preferably it is selected from sodium hydrogen phosphate, sodium dihydrogen phosphate and sodium hypophosphite, and most preferably from sodium dihydrogen phosphate. 11. The polycondensate according to claim 1, in which the non-polymeric polyol containing from 3 to 6 hydroxyl groups, if present, is a linear, branched and / or cyclic, saturated or unsaturated carbon or, in particular, hydrocarbon compound containing from 3 to 18 carbon atoms, in particular from 3 to 12 or even from 4 to 10 carbon atoms, and from 3 to 6 hydroxyl (OH) groups, as well as possibly containing one or more oxygen atoms introduced into the chain (ether functional group ), and preferably is linearly or a branched saturated hydrocarbon compound containing from 3 to 18 carbon atoms, in particular from 3 to 12 carbon atoms or even from 4 to 10 carbon atoms, more preferably selected from triols, tetraols, pentols and hexols, and even more preferably selected from glycerol , pentaerythritol, diglycerol and sorbitol, and mixtures thereof, and most preferably is individually glycerol. 12. The polycondensate according to claim 1, in which: - cyclodextrin (s) is (constitute) from 10% to 70 mass% relative to the total mass used in the synthesis of polycondensate, - polycarboxylic acid (s) and / or its derivatives in the form of an ester, acid anhydride or acid halide is from 5% to 40 mass% relative to the total mass used in the synthesis of polycondensate, - the polymer (s) of the thermoplastic polyol is from 10% to 50 mass% relative to the total mass used in the synthesis of polycondensate, - cyclic anhydride (s) of polycarboxylic acid, if present, is from 0.1% to 10 mass% relative to the total mass used in the synthesis of polycondensate, - the esterification catalyst (s), if present, is from 0.1% to 5 mass% relative to the total mass used in the synthesis of polycondensate, - non-polymeric polyol (s) containing from 3 to 6 hydroxyl groups, if present, from 1% to 30 mass% relative to the total mass used in the synthesis of polycondensate. 13. The polycondensate according to claim 1, which is obtained in the form of a powder. 14. The polycondensate according to claim 1, which is obtained at a temperature of from 150 to 180 ° C. 15. The polycondensate of claim 2, wherein the ratio of the number of moles of polycarboxylic acid to the number of moles of cyclodextrin is from 0.6 to 4. 16. The polycondensate of claim 15, wherein the ratio of the number of moles of polycarboxylic acid to the number of moles of cyclodextrin is from 0.7 to 3. 17. The polycondensate according to claim 3, having an acid number expressed in mg of potassium hydroxide per g of polycondensate, which is from 20 to 250. 18. The polycondensate according to claim 17, having an acid number expressed in mg of potassium hydroxide per g of polycondensate, which is from 40 to 180. 19. The polycondensate according to claim 4, characterized in that it exhibits a degree of swelling in water, measured at 20 ° C, which is from 300% to 900%. 20. The polycondensate of claim 5, wherein the cyclodextrin is β-cyclodextrin. 21. The polycondensate of claim 8, wherein the thermoplastic polyol is selected from hydroxypropyl cellulose and hydroxyethyl cellulose. 22. The polycondensate of claim 10, wherein the esterification catalyst is selected from sodium hydrogen phosphate, sodium dihydrogen phosphate and sodium hypophosphite. 23. A method of obtaining a cyclodextrin polycondensate, as defined in any of the preceding paragraphs, characterized in that at least one cyclodextrin, at least one polycarboxylic acid and / or its derivative in the form of an ester, acid anhydride or acid halide, at least one thermoplastic polyol polymer and, optionally, at least one cyclic polycarboxylic acid anhydride, different from the previous polycarboxylic acid anhydride, and / or at least one kata an esterification ister and / or at least one non-polymeric polyol containing from 3 to 6 hydroxyl groups is mixed in an apparatus operating with a shear force sufficient to bring the mixture into a thermoplastic state and operating at a temperature of from 100 to 250 ° C . 24. The production method according to p. 23, characterized in that all the ingredients are placed, in one stage, in an extruder at a temperature of from 110 to 200 ° C, preferably from 120 to 190 ° C, preferably from 150 to 180 ° C. 25. The use of cyclodextrin polycondensate according to any one of paragraphs. 1-22, as an exciting agent. 26. The use of claim 25 as an agent for capturing a substance or mixture of substances selected from: i) substances capable of polluting the environment, ii) substances capable of adversely affecting the consumption product, iii) substances capable of degrading under the influence of atmospheric factors or in contact with one or more ingredients of the composition, iv) substances capable of causing undesired reactions in a keratin substance, in particular a human keratin substance, v) beneficial agents. 27. The application of claim 26, wherein the beneficial agents are selected from: i) fatty substances ii) flavoring substances and / or flavor enhancers, iii) aromatic substances iv) pharmaceutically active ingredients, (v) cosmetically active ingredients. 28. The application of claim 26, wherein the substance or mixture of substances is capable of causing undesired reactions in a keratin substance, in particular a human keratin substance, is selected from: i) molecules of bad smelling substances, in particular molecules of bad smelling substances of body fluids, ii) components of human sweat, iii) sebum components. 29. A consumer product containing at least one cyclodextrin polycondensate according to any one of paragraphs. 1-22. 30. The consumer product according to claim 29, which is a cosmetic or dermatological composition containing a physiologically acceptable medium. 31. A method for the cosmetic treatment of odors of human sweat and / or body odors, comprising applying to the surface of a keratinous substance of a person a composition comprising, in a physiologically acceptable medium, at least one cyclodextrin polycondensate as defined in any of the preceding claims. 1-22. 32. Non-therapeutic cosmetic method for the care and / or purification of human keratinous substances, fatty, or prone to fat, comprising at least one stage of local processing of the specified keratinic substances, compositions containing, in a physiologically acceptable medium, at least one cyclodextrin polycondensate as defined in any one of claims. 1-22.